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One-Day Itinerary

One Day in Chicago: The Perfect Itinerary

chicago day trip itinerary

TripSavvy / Cory Giguere 

Don’t let the winds blowing off Lake Michigan scare you— Chicago , the Windy City, is a metropolis full of culture and history. Sightseers flock to the birthplace of the skyscraper, for its: Michelin-starred restaurants ; major league sports teams; world-class theater, dance, music, and film; festivals; 26 miles of lakefront; well-curated museums ; and stellar shopping. Chicago is also full of green spaces that are worth exploring like Chicago Botanic Garden and The Morton Arboretum . No matter what you do, or where you go, you’ll appreciate the city’s midwestern allure, with a bit of urban edginess. 

This walking-city, with 2.7 million residents, utilizes speedy public transportation to get from point A to point B. As you get on and off the elevated rail, or L, you’ll notice a mashup of sleek and modern buildings with loads of history and nods to the past throughout Chicago’s 46 historic districts and 77 vibrant neighborhoods. Chicago River architecture tours or walking excursions will highlight the City of the Big Shoulders’ storied past—the rise of a transportation hub, the Great Chicago Fire, the World’s Columbian Exposition of 1893, prohibition era, and Chicago’s public enemy number one, Al Capone .

Whether you’re a first-time visitor to the Second City, or a seasoned local, peruse this 24-hour itinerary for an across-the-board exploration of what Chicago has to offer, highlighting must-see tourist spots as well as local neighborhood gems.

The Night Before

Night: Arrive in Chicago and check-in to your accommodations—there are 119 hotels to choose from in the central business district. Luxurious options in the city include: Waldorf Astoria Chicago , Four Seasons Hotel Chicago (the spa here is fantastic), The Langham Chicago , Park Hyatt Hotel Chicago , and The Peninsula Chicago (the lobby is exquisite). Other well-located alternatives are Hotel Zachary , near Wrigley Field (the second oldest ballpark in Major League Baseball); Hotel EMC2 , with a robot concierge; and InterContinental Chicago Magnificent Mile , with a hidden hole in the wall for a prohibition-era alcohol stash.

Intrepid families that would love to spend a night at one of the museums can bring a sleeping bag and a sense of adventure to Adler Planetarium’s Astro Overnights, the Field Museum’s Dozin’ with the Dinos, Overnights at the Shedd Aquarium , or the Museum of Science and Industry’s Science Snoozeum.

7:30 a.m.: Take advantage of waking up in one of the best cities in the world and go for a leisurely jog or a fast-paced walk along the Chicago Riverwalk, a 1.25-mile stretch that has Adirondack chairs toward the east end for catching your breath. You’ll pass by stunning architecture, art installations, and boats cruising up and down the Chicago River. Continue on to the paved Chicago Lakefront Trail, along Lake Michigan, which runs from Ardmore Street on the north side to 71st Street on the south side, traversing many historic neighborhoods like Lincoln Park, South Loop, Bronzeville, and Hyde Park. The skyline views, when you’re facing south, are incredible, especially at this time of day. You can see Navy Pier , Chicago’s most-visited attraction, from the trail, with its Centennial Wheel rising high in the sky. For great people watching, linger at Oak Street Beach for a beat. (The 606, in Logan Square, is another great place to run that is popular with locals. This neighborhood park was created on the old elevated Bloomingdale train line—similar to New York’s High Line .)

10 a.m.: Make your way to Cindy’s for brunch, located on the rooftop of the famed Chicago Athletic Association Hotel , formerly a men-only social club. You won’t believe the terrace view of Millennium Park, The Art Institute of Chicago (the “Historic Route 66” begins in front of the Art Institute), Lake Michigan, and the shops and restaurants below at street level. Make reservations well in advance—this place is always packed—and order the avocado toast and the roasted vegetable strata. Save room for the house-made vanilla mascarpone Danish, with roasted cherries.

Noon: Across from Cindy’s is the 24.5-acre Millennium Park , a well-loved public space that is home to the Jay Pritzker Pavilion, Cloud Gate—the Instagram-worthy shiny bean-shaped sculpture, Crown Fountain, and Lurie Garden. Millennium Park Campus is also where you’ll find Maggie Daley Park, the best place to go if you have kids in tow.

1:00 p.m.: Meet up with Chicago Architecture Foundation ’s guide to learn about Chicago architecture and history on a two-hour walking tour through the city. You’ll get the lay of the land and learn more than you dreamed possible to enrich your time spent in the city. On the way, caffeinate with a cold brew or bulletproof coffee at Goddess and the Baker , located at Wacker Drive and Lasalle Street.

3:00 p.m.: You can’t leave Chicago without weighing in on which pizzeria serves up the best slice of deep dish . Is it Giordano’s, Lou Malnati’s, Pizzeria Due, Gino’s East, Piece, or Home Run Inn? You decide.

5:00 p.m.: Walk off that heavy pizza and stroll along the Magnificent Mile , a 14-block stretch of Michigan Avenue—from the Chicago River to Oak Street—that is mecca for shopping. Here, you’ll find malls and boutiques full of designer threads as well as affordable clothing brands. Keep in mind, this area is usually congested with shoppers, especially around the holidays and on weekends, so it’s best to plan out which shops you’d like to see in advance. Take a few snaps in front of the famous Chicago Water Tower , built in 1869, on the north end of Michigan Avenue. If shopping isn’t your thing, why not take an Intro to Climbing class at Chicago’s Brooklyn Boulders , located in Greek Town, west of the river, near Ogilvie Transportation Center?

6:00 p.m.: Take the high-speed elevator up to the observatory at 360 Chicago (formerly The Hancock Observatory) where, on a clear day, you can see Michigan, Indiana, and Wisconsin. Test your fear of heights on the Skydeck open-air viewing deck and see Michigan Avenue, 1,000-feet below, in the TILT attraction.

7:00 p.m.: You’ll want to experience Chicago’s diverse theater, music, or dance scene—the city has more than 250 theaters, 225 music venues, and 200 dance companies. Long-standing theaters include: The Second City in Old Town, Goodman Theatre and Chicago Theatre in the Loop, Music Box Theatre in Lakeview, Blue Man Group at Briar Street Theatre in Boystown, Steppenwolf Theatre Company , Chicago Shakespeare Theater , Lookingglass Theatre Company , just to name a few. And, of course, Chicago has no shortage of great live music, especially blues and jazz music (the term “jazz” was coined in Chicago). Music festivals like Chicago Blues Festival, Chicago Jazz Festival , Lollapalooza , Pitchfork Music Festival and Riot Fest are well-attended and loved in this city. Not to be missed is Chicago Symphony Orchestra , Lyric Opera and the Joffrey Ballet . The Harris Theater for Music and Dance is home to major Chicago dance troupes. You can’t do it all of course, so pick wisely and plan on returning to Chicago for another go-round in the future.

10:00 p.m.: For late-night noshes, local beers, and inventive cocktails, pop over to Lincoln Park’s Broken Barrel Bar , with Chef Bryant Anderson at the helm. This place is great for that non-touristy neighborhood feel that Chicago is really known for and you’ll get a sense of what one Chicago community is like by playing a game of bags or hanging around in the beer garden. Other great options, with completely different environments are: The Berkshire Room in River North, Milk Room in the Loop, The Aviary in the West Loop , The Violet Hour in Wicker Park, River Roast on the Chicago River, and The Optima in Old Town.

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24-hours-downtown

24 hours in downtown Chicago

With just one day to explore, you can make the most of your time with iconic, one-of-a-kind attractions and city experiences. Mix and match from the 10 itinerary stops below to create your perfect combination of restaurants, parks, museums, music, clubs, and rooftop views.

How to spend 24 hours in downtown Chicago: Stop 1: Visit Art Institute of Chicago Stop 2: See “The Bean” at Millennium Park Stop 3: Wander the Chicago Cultural Center Stop 4: See Buckingham Fountain at Grant Park Stop 5: Explore the lakefront Museum Campus Stop 6: Enjoy the view at SkyDeck Chicago Stop 7: Hear local legends at jazz & blues clubs Stop 8: Admire colorful street art Stop 9: Take an architecture river cruise Stop 10: Relax on the Chicago Riverwalk

Stop 1: A museum fit for Ferris Bueller

The Art Institute of Chicago

Anyone who loves the movie Ferris Bueller’s Day Off will know the Art Institute of Chicago . As you walk along Michigan Avenue, you’ll be greeted by two enormous bronze lions at the museum’s grand entrance. 

Once inside the Art Institute, you’ll experience one of the largest and oldest art museums in the United States, and one of the most expansive collections of Impressionist and Post-Impressionist artwork outside of the Louvre in Paris.

Make sure you visit the critically acclaimed Modern Wing, too, which houses an extraordinary collection of modern and contemporary masterpieces by Chagall, Dali, Matisse, Picasso, Pollack, Warhol, Magritte, and more. If you’d like to indulge in a little fine dining afterwards, head to Terzo Piano  on the Modern Wing’s upper level. In the summer, you can dine on the Bluhm Family Terrace amid rotating art installations and fabulous views of Millennium Park.

Stop 2: A giant bean and enormous rock climbing wall

Watch your kids climb all the way to the top at Maggie Daley Park

Take the Nichols Bridgeway from the Modern Wing across to Millennium Park   and you’ll find an unprecedented combination of stunning architecture, sculpture, and landscape design all in one place. From the towering faces of Chicagoans at Crown Fountain to your own face reflected in the polished steel surface of Cloud Gate , aka “The Bean,” you’ll see exactly why Millennium Park is one of Chicago’s top bucket list contenders.

Exit Millennium Park via the BP Bridge, a 935-foot-long winding walkway that offers incomparable views of the Chicago skyline, Grant Park ,  and Lake Michigan. On the other side of the bridge sits Maggie Daley Park , a spectacular green space with massive rock-climbing walls, mini golf, picnic groves, tennis courts, and an amazing play garden. In the winter, the park’s in-line Skating Ribbon is transformed into a unique, meandering ice skating path. There’s another ice-skating rink at McCormick Tribune Plaza in front of “The Bean.” Over the summer months, ice makes way for a scenic outdoor patio right on the plaza.

Stop 3: A Tiffany jewel in the crown

chicago day trip itinerary

On the corner of Michigan Avenue and Randolph Street, you’ll encounter the Chicago Cultural Center , a neoclassical landmark that houses the largest Tiffany stained-glass dome in the world. This stunning building is a humanities haven, with concerts, dance performances, theatre productions, films, lectures, art exhibitions, tours, and family events scheduled throughout the year — and all for free.

Stop 4: A waterfront landmark

Chicago's Buckingham Fountain lit up with spouting water

Walking south and east through Grant Park , you’ll find yourself in the heart of a 319-acre green space, anchored by mesmerizing Buckingham Fountain . This Chicago landmark, one of the largest fountains in the world, was dedicated in 1927 and inspired by the Latona Fountain at the Palace of Versailles. Typically from early May through mid-October, the fountain produces a dazzling water display for 20 minutes every hour throughout the day. During these displays, a center jet shoots water to a height of 150 feet, with lights and music beginning at dusk.

Stop 5: Explore museum campus

Shedd Aquarium Chicago kids

Walking south from the fountain, head to Chicago’s legendary Museum Campus. This gorgeous green space directly on Lake Michigan and is home to three of the city’s most popular museums. The Field Museum will be the first museum you encounter and well worth a trip inside. It’s home to thousands of natural history artifacts spanning thousands of years, including the largest dinosaur ever discovered.

Shedd Aquarium  sits right next door. Here, in one of the largest aquariums in the world, you’ll meet 32,000+ aquatic creatures, including beluga whales, dolphins, sea otters, sea lions, penguins, stingrays, and sharks.

Just beyond the Shedd is Adler Planetarium , which, upon opening in 1930, became the first planetarium in the Western Hemisphere. The building is more than a museum; it’s a laboratory, a classroom, and a community exploring the universe together. Visitors flock to the Adler to experience interactive exhibits, live planetarium shows, hands-on educational programs, and world-class collections.

Stop 6: Views from towering heights

Tours & Sightseeing Hero Image

Sky deck at Willis Tower invites you to step on The Ledge, a glass box that extends approximately four feet from the building’s facade — over 1,300 feet above ground level. Willis Tower is one of the tallest buildings in the world, and, as you might expect, the views from Skydeck are amazing.

Stop 7: A music mecca or two

Buddy Guys Legends

Two neighboring music clubs, one blues and one jazz, are must stops for the full Chicago experience. Buddy Guy’s Legends   was made famous around the world by its namesake, Grammy-award-winning blues guitarist Buddy Guy. There’s live music every night of the week, with free acoustic shows during lunch and dinner hours. Established in 1947, Jazz Showcase has hosted some of the greatest names in the business. The 170-seat club features local, national, and international acts nightly.

Stop 8: Picasso and Chagall on the street

chicago day trip itinerary

Public art lives large in Chicago. And nowhere is this better seen than at Daley Plaza   and nearby Chase Tower Plaza. Picasso’s 50-foot-tall untitled sculpture takes center stage at Daley Plaza. When it made its debut in 1967, The Picasso , as it’s known, caused some controversy, with people comparing it to a large insect or baboon. Today, it’s an enduring symbol of Chicago itself.

At Chase Tower Plaza, Chagall’s monumental The Four Seasons   mosaic mural represents the arrival of spring, summer, winter, and fall. It’s composed of thousands of inlaid fragments in over 250 colors, and was created in Chagall’s studio in France before being dedicated to the city in 1974.

Stop 9: Architectural history on the waterfront

Boat on the Chicago RIver

Head toward the river and you’ll find One Illinois Center, the Mies van der Rohe-designed home of the Chicago Architecture Center . Check out the to-scale skyscraper models in the Skyscraper Gallery and the approximately 4,200-piece immersive City of Chicago model on the main level, before picking the perfect architectural walking, bus, or boat tour at the center’s box office.

The Chicago Architecture Foundation Center River Cruise aboard Chicago’s First Lady  is a crowd pleaser, and was voted Chicago’s #1 tour by TripAdvisor users. It’s led by knowledgeable Chicago Architecture Center docents who’ll tell you the fascinating history behind approximately 50 of the city’s iconic downtown buildings.

Stop 10: Relax along the river

chicago day trip itinerary

The award-winning Chicago Riverwalk  is a 1.25-mile pedestrian stretch filled with coves, restaurants, bars, museums, public art, kayaking, boat excursions, bird-watching, fishing — and Art on theMART, the largest video projection art installation in the world. Illuminating over 2.5 acres of theMART’s river-facing façade, you can view the work of notable video artists from 7:15 – 9:15 p.m. Wednesday through Sunday, from March through April, and daily from May through December

Inside tip: Take a free Chicago Greeter tours

See Chicago like a local, with a local, with a free, customizable Chicago Greeter tour . Pick your neighborhood, theme, and language, then team up with a friendly guide who’ll show you both classic Chicago and its off-the-beaten-track gems. Book today .

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One Day in Chicago Itinerary – How to Spend a Perfect Day in Chicago, Illinois

Chicago is one of the most vibrant cities in the world – combining an eclectic mix of sports, architecture, music, food and art. Located on the shores of Lake Michigan, the towering skyscrapers stand proudly over the beaches of Lake Shore Drive and the outdoor spaces of Millennium Park. Whether you want to enjoy a hot dog in the outfield at a Cubs game or visit the world-renowned Art Institute of Chicago, this city provides unlimited activities for even the most discerning travelers. You could never see all of Chicago in a single day but this itinerary will take you to its top destinations.

One day in Chicago Itinerary

GUEST POST BY DEBORAH JANOWSKI BLOG: Relaxed Nomad

What’s the best time to visit Chicago?

Chicago is known as the windy city  and winter means it can be very, very cold, so the best time to visit Chicago is during the summer when the weather is a beautiful eighty degrees and sunny – and the outdoor parks and streets are alive with activity.

Chicago Skyline

What’s good to know about Chicago?

Chicago is very compact, so the majority of sights are located in the downtown area which makes it easy to see a lot in a short period. North of Wacker Drive is where you can find most of the stores and restaurants of Michigan Avenue and south of Wacker Drive is Millennium Park , the Art Institute of Chicago and Soldier Field.

Chicago Millenium Park

One Day in Chicago Itinerary

Store your luggage:  LuggageHero allows you to store your luggage for as long as you want to. If you are there only for a day, or waiting for a check-in, this sounds like a perfect option!

Follow this guide and make the most of your trip even if you’re short on time. These are the top sights and things to do during your one day in Chicago.

Millennium Park, Art Institute of Chicago

Begin your morning by walking Millennium Park . This park is home to the Buckingham Fountain, the Cloud Gate sculpture (often referred to as The Bean), large outdoor modern sculptures and gardens.

Chicago Cloud Gate

After touring the park, t he Art Institute of Chicago is located at the southern end. The museum houses some of the most famous works of art in the world including Grant Wood’s American Gothic and Edward Hopper’s Nighthawks. After perusing the art, t he Gage across the street is a local favorite for lunch complete with Scottish Eggs and Poutine Fries.

Art Institute of Chicago

Wrigley Field

If you like sports, you may want to try to head a bit north to visit the historic Wrigley Field and catch a Cubs game on a beautiful afternoon. The stadium is home to a number of Chicago staples including craft sausages, hot dogs and buffalo chicken fries. And Chicago fans are typically very welcoming and happy to talk with visitors about their love of the city and their home teams.

Wrigley Field

Architectural Boat Tour

Or, if you don’t particularly like baseball or there is not a game in town the day you are visiting, you can go on one of the many architectural boat tours in the harbor of Lake Michigan to learn about the history and sights of the Chicago skyline from the water while enjoying a cool summer breeze.

Chicago Architectural Boat Tour

Hancock Tower, Michigan Avenue

Many visitors will visit the Skydeck where you can purchase tickets to stand in a glass outcropping to see the entire Chicago area from the top of the Sears Tower. However, locals prefer to visit the Hancock Tower and the Signature Lounge on the 96th floor. As the sun begins to set, you can enjoy a glass of wine while enjoying a 180-degree view from your own table. Before or after visiting the tower, there is also time to stroll along the famed Michigan Avenue, which is always crowded with visitors from around the world and a large number of boutiques and stores.

Signature Lounge Chicago

Like any major city, there are simply too many places to eat in Chicago to pick just one. If you want to enjoy a Chicago pizza , you can stop at any of the pizza locations in the Michigan Avenue area. We won’t recommend one over the other (Lou Malnati’s, Pizzeria Uno, Bartoli’s, etc.) as that would simply lead to an argument with most Chicagoans over which is the best.

If you want something unique, you can enjoy dinner at the RL Restaurant right around the corner from the Hancock Tower. The RL Restaurant is attached to Ralph Lauren’s signature store and specializes in burgers and corned beef.

If you want something more lively, you can head over to Gibson’s on Rush Street by cab and either sit around the piano singing songs with the locals or head upstairs for a steak dinner.

Blues Music

After dinner, no trip would be complete without enjoying live Chicago blues music . This can entail a trip south to Buddy Guy’s Legends by Millennium Park. Or north to Kingston Mines in Lincoln Park. But whichever way you travel, cabs are plentiful and rides are short.

Where to stay in Chicago?

Park Hyatt Chicago

Park Hyatt Chicago

800 North Michigan Avenue, Chicago

Located in the heart of downtown Chicago, Park Hyatt Chicago features sophistication and luxury for both business and leisure travelers. The interior decor combines timeless elegance with a prominent art and modern amenities.

BOOK A ROOM HERE

Aloft Chicago City Center

Aloft Chicago City Center

515 North Clark Street, River North, Chicago

The Aloft Chicago City Center is a modern boutique hotel located in the heart of downtown Chicago’s in trendy River North neighborhood. It features a modern fitness center and business center, as well as the lounge with a pool table. It’s walking distance to Millennium Park and many other popular sights.

Kinzie Hotel

Kinzie Hotel

20 West Kinzie Street, River North, Chicago

Kinzie Hotel is an upscale boutique hotel located in Chicago’s River North district, only a short walk to the famous Magnificent Mile. The hotel features fully designed, bright and modern rooms for a perfectly comfortable stay for all types of travelers.

Hostel Stay

Chicago Getaway Hostel and  HI Chicago Hostel  are two of the best hostels in the city, perfect for young travelers who want to socialize with others and meet fellow travelers. You can still be close to the city center and all the great sights without spending a fortune on the accommodation.

Chicago Getaway Hostel

DAY TRIPS FROM CHICAGO

Day trips from Chicago are always a great idea if you have the time. This big city certainly offers a lot, but heading out of town certainly has its advantages, too. There is plenty to see, and you can even visit another US city rather painlessly. The options are numerous, and here’s what you’ll want to check out.

A day trip from Chicago to Milwaukee is a great solution for tourists who want to experience as many US cities as quickly as possible. It will only take you about an hour an a half to get there, be it by car or by train. There are loads of very interesting museums to see ( Harley Davidson Museum first comes to mind), great food to enjoy and delightful people to meet. You certainly won’t regret visiting this lively city.

A short ride west from Chicago (about 30 minutes) is Oak Park. Now, this quaint little town for those who want to enjoy arts and especially architecture. The famous architect Frank Lloyd Wright was so prolific here that he has his own district, but there are also many other types of art worthy of checking out in this quaint little town. This is a vibrant, diverse and chilled out community and a perfect place to spend your day.

Indiana Dunes National Lakeshore

If you want to enjoy some beautiful nature, head to Indiana Dunes National Lakeshore. Yes, you will have to cross the state line, but it’s only about an hour’s drive away from Chicago. This is an excellent place for bird watching , as there are literally hundreds of different kinds of birds that migrate through here. Swimming, hiking and fishing are also some of the things you can do, so if you want an active outdoors vacation, this part of Lake Michigan is definitely for you.

Last, but most certainly not the least, you can head on a day trip from Chicago to Holland. As you can see from its name, this little town is very proud of its Dutch heritage. And it shows! This place is home to the Tulip Time Festival , and you can see these beautiful flowers wherever you look. Not only that, but you can also enjoy some excellent Dutch cuisine and absolutely beautiful houses and cobblestone streets . This really is an escape into a dreamworld!

Extra tips for visiting Chicago

– We recommend against using a rental car . Parking in Chicago is difficult and taxis are everywhere and very convenient, so it is quite easy to walk and catch a quick ride anywhere in the city.

– Traffic to and from the airports in Chicago can be very congested,  so plan your trips accordingly.

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If you have any other propositions for this One Day in Chicago Itinerary feel free to share it in the comments below!

Make sure you have everything you need

What to pack for your next trip.

Make your next trip as simple and as enjoyable as possible by packing smart. It’s amazing how much stress top travel items can save you, so choose carefully. Things like lightweight travel backpacks, for example, are ideal for short trips and allow you to move around with ease, and a passport holder will make sure you keep your documents safe at all times. Check our travel checklist guide for 2021 to make sure you haven’t missed anything, and travel to your next destination in style and with maximum comfort.

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RelaxedNomad

Deborah Janowski

Deborah runs the travel website, RelaxedNomad, which specializes in sharing itineraries, notes and travel plans for entire areas of the country and road trips. One of her goals is to make traveling easier for families while finding truly unique activities in unusual places.

Great! Hope you can check out my blog re: Chicago as well 🙂 Spent a few hours there but it was worth it!

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Home » North America » Chicago

CHICAGO Itinerary • MUST READ! (2024)

With incredible works of public art scattered all around the city and free access to many of its museums and art centers, Chicago is a cultural hub! It’s also America’s third-largest city and the birthplace of the modern skyscraper.

This immense and beautiful city has a vibrant outdoor culture, with many activities and attractions to enjoy. You’ll find unique and delicious cuisine, fantastic outdoor fun, and great local sports. We’ve put together an itinerary for Chicago which covers all the best attractions in the city!

Pack your walking shoes and prepare to visit some iconic places. With one of the most recognizable skylines in the world and a community welcoming to travelers, you’ll have the time of your life!

chicago day trip itinerary

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Best Time To Visit Chicago

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Chicago is known as the windy city! However, many days outside of winter are balmy and perfect. All seasons are distinctly represented in Chicago. The city has hot, frequently humid summers, and wet, cool springs. Fall can be pleasantly temperate fall with a cold winter to follow. When you choose to go depends on your seasonal preferences!

when to visit Chicago

Wondering when to visit Chicago? Most tourists plan their vacation in Chicago during the summer when it’s hot. However, we suggest going in early autumn or late spring, when the crowds are much calmer and the weather is mild.

Unfortunately, many of Chicago’s outdoor attractions close for the frigid winter season (November – March), so keep that in mind if you are wanting to visit during this period. It is a great time to visit if you’re coming to Chicago for its many indoor activities and don’t mind the cold!

chicago day trip itinerary

With a Chicago City Pass , you can experience the best of Chicago at the CHEAPEST prices. Discounts, attractions, tickets, and even public transport are all standards in any good city pass – be sure invest now and save them $$$ when you arrive!

Chicago is one of the largest cities in America, with sprawling neighborhoods and lots to do in all of them. Accommodation ranges from top luxury on the Magnificent Mile to low-budget hostels in Chinatown. You can find a place for any budget and a range of interests!

where to stay in Chicago

The best place to stay in Chicago is undoubtedly Downtown Chicago/The Loop. It’s central and home to Chicago’s most prolific and most important landmarks, you will hardly need to leave the area and will save time and costs on public transportation! It’s an especially good idea if you’re only spending two days in Chicago.

The Loop is designed in a grid pattern, making it very navigable to first-timers. No matter where you stay in the neighborhood, you’ll find great restaurants and things to see no more than a block away.

If you’re interested in staying somewhere a little more obscure and experiencing a different side of Chicago, find a place in West Loop! It’s a great neighborhood for foodies, and there are many galleries and cafés nestled away, far from the Chicago skyscrapers (but not too far).  

There are hotels, hostels, hovels and Airbnbs in Chicago so suit every budget. In fact, if you are really on a budget, you can find some cheap and comfy motels in Chicago .

If you’re looking for something that better suits you, you can also have a look at our more detailed guide on where to stay in Chicago !

Best Hostel in Chicago – Hi Chicago

chicago itinerary

This beautiful, expansive hostel is located in the heart of Downtown Chicago. It’s a great place to meet fellow travelers. It includes a pool table, bar, ping-pong table, and other great general areas.

Rooms are clean, comfortable, and gender-separated. Best of all, you get a large breakfast, a spacious locker, and guided tours of the city, all free!

To see more hostel options, check out our top picks for hostels in Chicago .

Best Airbnb in Chicago – Modern loft for 2

Modern loft for 2, Chicago

With this basic, convenient and well-priced studio apartment, you have access to a comfortable, queen size bed, full kitchen, on-site laundry facility, free wifi, and an awesome host who will recommend you places to visit, attractions to see in Chicago.

Best Budget Hotel in Chicago – Best Western Grant Park Hotel

chicago itinerary

A short walk from some of Chicago’s top attractions, this budget hotel is comfortable and fun. The rooms are clean, and the staff are helpful and knowledgeable. There’s an on-site restaurant, fitness center, and business center.

The beds are large, and if you book a room on one of the top floors, you’ll enjoy fantastic views over Chicago!

Chicago Itinerary

Chicago is not a very walkable city, as it is very large. However, walking within the neighborhoods is very doable. Most of the attractions and landmarks are centered in Downtown Chicago, so we suggest you go by foot here. Walking is also a great option because it allows you to see more of the people and culture of the city!

There are also fantastic public transport systems in Chicago. You can catch the L Train, which stops all over Chicago. It’s cheap and easy to use, navigable to first-timers and tourists.

Alternatively, you can take the bus. These stop right outside of most Chicago points of interest, making it ideal. However, it can be difficult for newcomers to navigate, and you may struggle to catch a bus that’s actually going right where you need to be!

Another great way to explore a few of Chicago’s neighborhoods is by bicycle. The city even has a Divvy bike-share system, which allows you to grab a bike from one of the hundreds of stations in the city. You can get a day-pass for these or a single fare.

The Art Institute of Chicago | Garfield Park Conservatory | Millennium Park | The Field Museum | Willis Tower Skydeck | Annoyance Theatre & Bar

On the first day of your Chicago Itinerary you’ll explore some of the city’s most iconic landmarks and beautiful places. Wear walking shoes – everything is within walking distance!

Day 1 / Stop 1 – The Art Institute of Chicago

  • Why it’s awesome: It’s one of the world’s greatest art museums.
  • Cost: $25; $35 for fast pass with audio guide .
  • Food Recommendation: Grab breakfast at the Corner Bakery Café.

Beautifully set out, the Art Institute is a fantastic experience and a great start to your Chicago Itinerary. Its displays are always rotating and being added to, so if you’ve been here years ago, don’t let that stop you from going again.

Admire the diverse range of art on display, broaching topics from South African Apartheid and resistance to Japanese life, to modern ideas of femininity and beauty. Attend talks on art and history in the museum! Get the audio guide and learn about the art and exhibitions as you go at your own pace.

You can spend the whole day here, but we suggest you spend 2-3 hours in the art museum. You can get a floorplan of the museum at the entrance, to help you plan your route and ensure you see everything you want to see.

Whether you love art or history or neither, this is a Chicago experience you don’t want to miss! You are permitted to take photographs, which is great, because you will really want to.

Day 1 / Stop 2 – Garfield Park Conservatory

  • Why it’s awesome: A green oasis under glass, it’s really something special.
  • Cost: Free, with an optional donation.
  • Food Recommendation: Find something delicious at the charitable restaurant Inspiration Kitchen.

Explore the Conservatory’s 2-acres of lush indoor display houses and exotic outdoor gardens! A beautiful getaway from the concrete jungle, the gardens host an incredible amount of flora from all over the world.

Visit the desert house for cacti and succulents, or the Palm House and Fern room, which evokes a swampy prehistoric landscape you can get lost in. In Sugar From the Sun, you’ll find botanic environments themes around water, air, sunlight, and sugar. Here you can learn about how plants make energy!

Garfield Park Conservatory

The outdoor gardens are a fantastic place to stop and enjoy a picnic, or a bit of lazing on the grass and soaking up the sun. These gardens have more to offer than grass though! The Monet Garden and Sensory Garden are wonderlands for the senses.

You can get a digital guide to the Garfield Park Conservatory for free on your phone, or just stroll around and enjoy the gorgeous plantlife. It is certainly one of the most beautiful places on our Chicago itinerary.

Day 1 / Stop 3 – Millennium Park & Cloud Gate

  • Why it’s awesome: The cultural and artistic hub of Chicago, the park is a must-see.
  • Cost: Free!
  • Food Recommendation: Pancake stacks at Wildberry Pancakes & Cafe.

If you’re planning a trip to Chicago, you have to visit Millenium Park. A unique town square, it’s leafy landscape is only a backdrop to state-of-the-art architecture, art and landscape design. Home to much of Chicago’s cultural offerings, you’re bound to find something amazing to do here. Family events, concerts, exhibitions, and tours are all  offered!

The Park’s unique, immense outdoor concert venue was designed by renowned architect Frank Gehry and spans much of the park. This is where you’ll find much of the activity!

Millennium Park & Cloud Gate

There is also, of course, Cloud Gate. Featured in many movies and pop culture references since its creation, Cloud Gate is the most recognizable Chicago landmark. The seamless sculpture reflects the Chicago skyline. And when you walk beneath it, it reflects you as well from myriad angles. Shaped similarly to a bean, it’s affectionately referred to by locals as ‘the bean’.

With so many artistic attractions, Millenium Park is a must-see even if you’re only spending two days in Chicago! It will charm you no matter what!

Day 1 / Stop 4 – The Field Museum

  • Why it’s awesome: The exhibitions are fascinating, and there’s so much to discover.
  • Cost: $24 – $38 ( Get an online ticket for fast access!)
  • Food Recommendation: Get Chicago streetfood classics at Kim and Carlo’s Hotdog Cart.

A brilliant museum for the natural sciences, Field provides an opportunity to learn and explore everything related to science and natural history! Discover dinosaurs, ancient artifacts, and groundbreaking scientific discoveries.

Research is always continuing at the museum’s extensive labs, leading global initiatives to discover more about our world. Spend a few hours exploring collections around different cultures from the past and present, fossils and meteorites that tell us about the earth’s history, and weird and wonderful animals!

The Field Museum

Everything is consistently updated and well-maintained, with amazing attention to detail. The T-Rex skeleton is the most complete one ever found! It’s quite a thing to behold.

Insider Tip: Even if you spent the whole day here you wouldn’t be able to see everything. So, decide what you really want to see at the outset, and give yourself three hours to take in all you can!

Day 1 / Stop 5 – Willis Tower Skydeck

  • Why it’s awesome: The best view over Chicago.
  • Food Recommendation: Try Chicago’s deep-dish pizza at Giordano’s, in Willis Tower.

With a glass-bottomed deck and impeccable views, there’s no better location to watch the sunset. This is a great place to take photos of Chicago, and of course, yourself with it. In fact, your ticket includes three professionally taken photographs!

Willis Tower Skydeck Chicago

The staff is very nice and helpful, elevating the experience. There is always a line, but it moves quickly. A typical skyscraper experience, the Willis Tower is worthwhile for unparalleled views. You will be able to see most of the other stops on your Chicago itinerary!

Day 1 / Stop 6 – Comedy at Annoyance Theatre & Bar

  • Why it’s awesome: Get a good laugh with Chicago locals.
  • Cost: $5 – $12
  • Food Recommendation:  Enjoy bar snacks or go to the nearby Ann Sather Restaurant.

A great way to spend the evening, Annoyance Theatre and Bar offers up a lot of laughs. With different acts every night, improv shows, comedy sketches, and musicals, there’s something for everyone, every night.

Comedy at Annoyance Theatre and Bar chicago

The Annoyance has played in comedy theatres all over America and has even been on TV, but their home-base is here in the windy city. Have a look at what’s on during your vacation in Chicago! You may even find a full-length cabaret or comedy musical.

With a fantastic festival-type atmosphere and tasty, well-priced drinks, you can’t go wrong. The performances are fun and creative, with a large cast and intimate setting! So grab a drink and find a seat. It’s a barrel of laughs.

chicago day trip itinerary

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Grant Park and Buckingham Fountain | Chicago Cultural Center | Museum of Science and Industry | Navy Pier | Wrigley Field | Magnificent Mile | Jazz at Blue Chicago

On day two of your itinerary for Chicago, you’ll see and do even more! Prepare to eat amazing food and enjoy some of Chicago’s best cultural offerings.

Day 2 / Stop 1 – Grant Park and Buckingham Fountain

  • Why it’s awesome: One of the biggest parks and fountains in the world!
  • Food Recommendation: Get some creative hot dogs at Devil Dawgs on State.

Surrounding the Millenium Park and extending far beyond it is Grant Park. This giant public park is affectionately referred to as ‘Chicago’s front yard’, and the first stop on your Chicago itinerary’s second day. Located in the central business district, you can stroll through and find hundreds of sculptures and public works of art.

Grant Park and Buckingham Fountain

Spend the early hours of the morning here while you wait for everything to open. (Chicago starts its days late). It’s a beautiful green space, and you’ll often find yoga sessions and ball games that anyone can join in!

While you’re here you have to seek out the Buckingham Fountain! Designed in 1927, the fountain is one of the largest in the world. It usually runs from 8 am to 11 pm daily, from May to October. Every hour, the Fountain produces an incredible 20-minute display! So if you’re visiting during this period, it is not to be missed.

Day 2 / Stop 2 – Chicago Cultural Center

  • Why it’s awesome: Beautiful building with exhibitions and events.
  • Food Recommendation: Grab a quick bite at Toni Patisserie & Cafe.

If you’re wondering what to do in Chicago for free, this is one of the best places to be! The architecturally stunning building is host to many wonderful things and none of them cost a thing.

Chicago Cultural Center

Find an art show, performance piece, musical event, or something else while exploring its Art Deco interiors.

The whole building is covered in beautiful mosaics. With a giant glass dome and ornate staircases, it’s a wonderful place to go even when nothing else is going on. It’s a lovely place to relax and take in some beauty.

Day 2 / Stop 3 – Museum of Science and Industry

  • Why it’s awesome: Impressive, interactive exhibits and great fun.
  • Food Recommendation: Italian food at Piccolo Mondo.

With interactive exhibits of all kinds, the MSI brings science to life. Descend into a coal mine, float outside the international space station in a virtual reality experience, and feel and the physics of a tornado created by man!

There is so much to do, you will be enveloped in the excitement of where we’ve been and where we’re going as a species and as a planet. There’s even a behind-the-scenes tour so you can explore how such a sprawling, impressive museum and scientific center works.

Museum of Science and Industry

One great new exhibit is Wired to Wear and is the first exhibit ever dedicated to wearable technology and where it can take us. Part of the future, it’s quite something to see this in the present and one of the best places to visit in Chicago .

Watch a film in the five-story, domed, wraparound movie theatre. The glory and intensity of nature is well-suited to such large-scale viewing. With hands-on experiments, interactive and interesting exhibits, and great, knowledgeable staff, MSI is a definite must-see on your trip to Chicago.

Day 2 / Stop 4 – Navy Pier

  • Why it’s awesome: A favorite for locals and tourists, this place is packed with things to do!
  • Food Recommendation: Find tasty seafood on the pier at Riva Crab House.

No ordinary pier, the Navy Pier has a wide and eclectic range of activities for solo backpackers in Chicago , families, couples, and friends.

Go for a ride on the iconic Centennial Wheel, with fantastic views over Chicago and Lake Michigan. Explore virtual reality or test your strength on the climbing wall. Navy Pier is also the primary departure point for many lake cruises and bus tours, so its the perfect place to go if you have a little more time than expected!

Navy Pier, Chicago

You’ll find public art and exhibitions, cultural attractions, a great variety of shopping opportunities, and of course, amazing restaurants. With such an eclectic range of activities, it could be the only thing on our Chicago Itinerary!

Day 2 / Stop 5 – Wrigley Field

  • Why it’s awesome: Baseball has been played here for over 100 years!
  • Cost: $13 – $154 for a game
  • Food Recommendation: Get something at the lively sports bar Murphy’s Bleachers.

Wrigley Field is a great American Ball Park with great, enthusiastic fans and a fun environment and vibe. Everything is well run with helpful and friendly security and staff, and well-maintained restrooms.

Across the street from the field, you can find plenty of sport-themed pubs and bars. Go after the game, and celebrate your team’s win or mourn their loss with people who are doing the same. It’s great fun, either way.

Wrigley Field

With over 100 years of iconic baseball games here, it’s a great place to spend a few hours and feel the spirit of Chicago. Recent renovations to the field add convenience to the ambiance of history, and as per tradition, you can buy hotdogs and beers at in-house vendors before taking your seat.

If you are more interested in the famous field than the game, you can go on a Wrigley Field tour! These last 90 minutes, and allow you to experience the beauty and charm of the historic field and learn about its captivating history.

Day 2 / Stop 6 – Magnificent Mile

  • Why it’s awesome: Admire skyscrapers and boutique shops in this world-famous upscale shopping district.
  • Food Recommendation: Mediterranean food at The Purple Pig.

Chicago’s premier commercial district, the Magnificent Mile, is where to go to get all your Chicago shopping done! More than this, it’s a great place to explore for its luxurious and posh atmosphere, with high-class fashion outlets, restaurants, and hotels.

We love window shopping in this district and people-watching! There are also numerous Chicago landmarks , including the Chicago Water Tower and the John Hancock Center. In fact, there are over 50 landmark structures here!

Magnificent Mile

Stroll down the long, beautiful avenue and admire so much of what makes Chicago a great international destination, right in one city center. It’s also nicknamed the Million Dollar Mile. Walking down it, you’ll understand why!

At night, everything lights up beautifully. Turn into a few taverns and art galleries for a laid-back and enjoyable cultural bar-hopping experience. Hopefully, you’ll meet a few locals!

Day 2 / Stop 7 – Jazz at Blue Chicago

  • Why it’s awesome: Fantastic blues and jazz and a great vibe
  • Cost: $10 – $12
  • Food Recommendation: Try Peruvian food at Tanta Chicago

Don’t worry if you’re not spending the weekend in Chicago! With live Chicago Blues seven nights a week, this is the perfect end to your two day itinerary in Chicago. This blues bar is the perfect place for it – a traditional ‘hole in the wall’ style establishment with well-priced drinks and an old-school atmosphere.

The world-renowned blues bar has been running since 1985 and is packed with locals and foreigners every night. Be sure to book beforehand or go early, and keep in mind that only adults over 21 may enter.

Jazz at Blue Chicago

Chicago Blues is an eclectic style of blues and jazz music which came about with the migration of African Americans from the South to the Midwest. The performances at Blue Chicago reflect this rich, powerful and difficult history, with great energy and a surplus of talent.

An important part of Chicago’s history and culture, this music is a celebration of life. to watch it and participate in continuing a proud musical tradition is really something special, and certainly one of the best things to do when spending a weekend in Chicago .

HI Chicago

This beautiful, expansive hostel is located in the heart of Downtown Chicago.

  • Free Breakfast

Chicago River Cruise | Chicago Food tour | Richard H. Driehaus Museum | Mob and Crime Bus Tour | Football Game at Soldier Field

If you’re spending three days in Chicago or more, these are the best activities and attractions to include in your Chicago itinerary! They’re a great way to explore the city and learn more about that unique Chicagoan culture.

Chicago River Cruise

  • Relax with a drink while cruising along the river.
  • Get insight into landmark buildings and marvel at the legendary architecture.
  • A 75-minute cruise on a state-of-the-art vessel.

Spend some time exploring one of the biggest Chicago attractions – the gorgeous river. On the architecture tour, you’ll cruise along all three branches of the Chicago River, spotting your favorite landmarks and learning about the city.

From the Navy Pier, you can catch numerous different types of cruises to suit your interests, like a dinner cruise, buffet cruise, or sport-themed cruise. You can also choose between different types of boats!

Our top choice is an architectural river tour, offering a captivating exploration of Chicago’s hidden gems and iconic landmarks. Among others, you’ll see Tribune Tower, the Wrigley Building, Marina City, and Willis Tower.

Relax and enjoy a drink from the bar. The cruise is 75-minutes, just enough time to relax and recover your energy before plunging back into Chicago’s central city hub!

Chicago is known as the birthplace of the skyscraper, and the home of modern American architecture. There is so much to learn and appreciate here. On the tour, you will have an expert guide, with facts, anecdotes, and answers about all of Chicago’s attractions!

Skip the ticket office and proceed directly to boarding by pre-purchasing your ticket online . One of the world’s most beautiful cities and a thriving modern metropolis, Chicago is well worth exploring this way.

If you want a more unique and exciting way to see the river and Lake Michigan, then consider chartering a yacht at an affordable price.

Chicago Food tour

  • Join a fun and enthusiastic foodie guide while touring Chicago.
  • Sample some of Chicago’s best culinary offerings.
  • Get insight into the art, architecture and everyday life of the metropolis.

This foodie Chicago walking tour is a simple classic – stroll through the city learning more about it from a local, while trying all of its best and most exciting foods.

Your guide is knowledgeable and friendly, and will tell you about much more than just the food! The city has so much to see and explore and has such an interesting history, including famous 1920s gangsters like Al Capone. It’s fantastic to explore it with a local, who knows all the best and worst things about the city. You can also get tips on how to explore Chicago’s food and dining scene some more if you’re interested.

Chicago Food tour

Chicago is famous for its American-style food innovations, like the deep-dish style pizza, and Chicago-style hot dogs. You’ll dig into some of these, among other foods! The tour lasts three-hours long, so you have ample time to eat and explore.

You will also get to meet new people on your tour, and enjoy your meals with new friends, laughing and chatting. It’s a great way to meet people while traveling, and also a great Chicago activity to do with friends and partners.

Richard H. Driehaus Museum

  • Explore an old mansion to see how the well-to-do lived during the Gilded Age.
  • Contemporary art contrasts with old-style luxury and decadence.
  • A guided tour is only $5 extra and contributes immensely to the experience.

If you’ve ever wondered what a home looked like in the late 19th century Art Deco period, this is the perfect place to be in Chicago! The museum was once the mansion of Samuel Nickerson and his family, a local banker. Now, after two restorations over the years, it explores the art, design, and architecture of that period to the present.

The permanent collection of period decorative arts suits their surroundings perfectly. Educational and cultural programs contribute to exhibitions which contextualize the Gilded Age and illuminate the vibrant history and culture Chicago.

Enjoy all the little details that make this museum stand out among much larger ones in the country. Each detail is unique, many inspired by locations around the world, others by jazz, music, and the urban culture of Chicago.

Richard H. Driehaus Museum

Year round the museum features rotating exhibits of modern and contemporary art, which contrasts with the location in interesting and beautiful ways. Spend a few hours here- the more you look, the more you will see.

The staff is also very passionate about their work, and the guides are knowledgeable. In fact, we certainly recommend the guided tour. There’s so much history here, beyond the aesthetic. You will want to learn more about it!

The Museum is located just steps from the Magnificent Mile, and is easy to find! It’s one of Chicago’s lesser-known attractions, so it’s a great place to relax and enjoy the peace.

Mob and Crime Bus Tour

  • Hear about how some of the world’s most famous mobsters conned their way through the city
  • Ride comfortably in a luxury bus, unaffected by Chicago’s unpredictable weather
  • Stake out notorious crime scenes and Chicago landmarks

An alternative way of experiencing Chicago is the Mob and Crime bus tour . It’s not for the faint of heart, though, exploring the sites of Chicago’s most famous and notorious crimes took place. It’s the perfect activity for those rainy or windy days when you can’t explore Chicago on foot.

See famous Chicago crime scenes from the 19th century through to modern times. You’ll learn about Al Capone, the Untouchables, the Chicago Mob, Terrible Tommy O’Connor, the Chicago Black Sox, Leopold and Loeb, Cap George Streeter, and more. You’ll also hear about some of the most daring heists in history!

Mob and Crime Bus Tour

Visit the historical criminal courthouse, an architectural landmark where some of the biggest cases were tried. Stake out other landmarks and learn about the darker, more criminal side of their history. For a time, gangsters ran Chicago . They are a large and important part of Chicago’s making and rich history.

You will also have the opportunity to leave the bus and walk the path that notorious Chicago gangsters John Dillinger and Hymie Weiss followed just before their deaths. It’s gory and intense, and a good deal of fun and intrigue.

Watch a Football Game at Soldier Field

  • Watch Chicago’s famous sport with enthusiastic fans.
  • Enjoy the iconic stadium, which has housed some of NFL’s most famous games.
  • More than just sports, you can watch live performances too.

On the third day of your itinerary in Chicago, go watch a football game! Most games are of course played on weekends.  The Bears, Chicago’s local team, have more regular-season and overall wins than any other NFL team. The team and the stadium have a rich history and a loyal following.

Join The Bears’ passionate fans, cheering on the home team, or watch a game with your favorite team! It’s the kind of good sports fun that doesn’t require you to have too much knowledge or enthusiasm for the game itself. Just enjoy the action and the great vibe!

Football Game at Soldier Field

Soldier Field is an iconic football stadium, easy to get around and has lovely, efficient staff. They’re attentive and organized, which is good in a 60,000 seat stadium! Interestingly, it is still the third-smallest stadium in the NFL.

Of course, the stadium also hosts massive concerts, so if you’re more interested in music than sports, have a look at what’s playing when you’re in Chicago .

So how safe is Chicago? Well most of Chicago is very safe for tourists, and you’ll have no trouble walking around and exploring during the day and night. There are, however, some neighborhoods that are better to avoid.

In these areas, gang violence and other criminal activities occur. They are quite clearly sketchy, though, and far from Downtown Chicago where you’ll spend most of your time exploring.

Pickpockets are reasonably common in very busy areas, and we suggest you keep your belongings firmly by your side. Muggings also occur, particularly at night. These can be avoided by staying on well-lit, well-populated streets and avoiding dark or dingy areas. Thieves sometimes operate on the subway, so it’s best to avoid it when out of peak times (7am-9am and 3pm-6 pm).

Neighborhoods to avoid, particularly at night, are the far West Side of Chicago, which has very few tourist attractions and the Fuller Park area. Parts of Downtown Chicago get empty at night, and therefore risky. North Side remains safe throughout the night, and you can walk comfortably here as long as you take the common-sense safety precautions.

Natural hazards do occur occasionally, but their safety risk tends to be low. There is, however, a higher risk during winter.

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chicago day trip itinerary

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Chicago is near to four different states! You can get to other great cities easily and explore the beautiful surrounding area on these day trips from Chicago.

Chicago to New York City Day Trip by Air

The best of the day trips from Chicago has to be New York by air! Fly to the Big Apple, where you’ll hop on a sightseeing bus and spot the greatest of New York’s world-famous landmarks, like the Statue of Liberty!

Chicago to New York City Day Trip by Air

The tour is very laid-back, with time to take in a show, do some shopping, or set out on a little extra sightseeing!

The tour includes a round trip from Chicago, a two-course lunch in Times Square, and your sightseeing bus trip. So different to Chicago and yet so close. It’s a fantastic part of the Chicago trip itinerary!

Tour of SW Michigan Wine Country from Chicago

Touring America’s beautiful wine country is the perfect day trip. You’ll tour the scenic countryside and visit three wine farms! Enjoy wine tastings at each of them and a gourmet lunch.

Tour of SW Michigan Wine Country from Chicago

Learn about winemaking and how the grapes in Michigan differ to those found in France’s Napa. Have a delicious meal overlooking a vineyard and enjoy some time walking through and learning about the farms.

The tour includes tastings, lunch, bottled waters, and a departure toast to start things off right! Get to know the people on your tour and enjoy leaving the city behind for a day.

Chicago Grand City Tour & 360 Chicago Observation Deck

This half-day tour of the city is one for the books! Travel through the north and south financial districts, admiring iconic buildings and sculptures. Experiencing the vitality and excitement of Chicago’s central hub.

Chicago Grand City Tour & 360 Chicago Observation Deck

Enjoy views of Lake Michigan and Jackson Park where the Colombian Exposition of 1893 was held to celebrate the founding of America.

You will also look out from the top of the John Hancock Building, and try to identify all four states! The tour is a great activity to bring friends who only have one day in Chicago.

If you fancy enjoying the windy cities magnificent skyline with a cold (alcoholic) drink, then try to find one of Chicagos rooftop bars – but drink responsibly!

Detroit: The Rise, Fall & Renewal Walking Tour

Fly to Detroit, where you can explore the very different American city with a walking tour before setting out on your own. On the tour, you’ll explore the social and economic upheavals of Detroit through its architectural landmarks, learning all about the city and its complex history!

Detroit The Rise, Fall & Renewal Walking Tour

The tour is a great introduction to the city. You’ll see some of the world’s tallest vacant buildings, and most beautiful modern landmarks. Chat with fellow tourists and a knowledgeable local.

Get tips on where to go next, and source out some of Detroit’s finest food at restaurants like Selden Standard.

Milwaukee Scavenger Hunt Adventure

Catch a short flight to Milwaukee, where you can join an exciting and fun scavenger hunt adventure! One of the best ways to explore the city, you’ll use your surroundings to solve clues and complete challenges.

Milwaukee Scavenger Hunt Adventure

You can stop and go as you please, and take as much time as you need, admiring and learning about the attractions as you go along. It’s a really laid-back trip, and a great experience for couples, friends, and families.

You use your smartphone to play the game and navigate the historic streets of Milwaukee, enjoying its modern and unique culture.

Active Roots Security Belt

Stash your cash safely with this money belt. It will keep your valuables safely concealed, no matter where you go.

It looks exactly like a normal belt  except for a SECRET interior pocket perfectly designed to hide a wad of cash, a passport photocopy or anything else you may wish to hide. Never get caught with your pants down again! (Unless you want to…)

Find out what people want to know when planning their Chicago itinerary.

How many days are enough in Chicago?

You’ll want to spend at least 3 days in Chicago, as the city is not very walkable. 4-5 days are ideal for seeing all the attractions and discovering the various neighbourhoods.

What should you include on a 3 day Chicago itinerary?

Don’t miss out on these Chicago highlights: – Millennium Park & Cloud Gate – Chicago Art Institute – Grant Park – Navy Pier

Where is the best place to stay for a weekend in Chicago?

Downtown Chicago is the best place to stay for a short trip. It’s super central, surrounded by the city’s top attractions, and bursting with eateries and nightlife.

What are the best day trips from Chicago?

The Chicago to New York City by Air day trip is the ideal way to spend an extra day. The Detroit Walking Tour and Milwaukee Scavenger Hunt Adventure are also very popular.

With so many world-class museums, sports centers, places of culture, music, food and fun, Chicago is one of the best cities in the world.

You can explore the history of the city, and the natural history of the world! Or stroll through its public parks, and later take in the earth’s most incredible flora. Chicago brings together elements of our whole world in ways unique to the vibrant city.

Even if you’re traveling on a shoestring budget, you can travel to Chicago and make the most of what the city has to offer! With our Chicago itinerary, you will certainly never have a dull moment.

Pack walking shoes, an umbrella, and be sure to bring your camera. You will want to capture the immense skyscrapers as well as the little details that make Chicago iconic!

chicago day trip itinerary

And for transparency’s sake, please know that some of the links in our content are affiliate links . That means that if you book your accommodation, buy your gear, or sort your insurance through our link, we earn a small commission (at no extra cost to you). That said, we only link to the gear we trust and never recommend services we don’t believe are up to scratch. Again, thank you!

Aiden Freeborn

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That’s a really thorough itinerary, kudos!

Sun Country Airlines is a low-cost airline. The airline offers a range of domestic and international flights to popular vacation destinations at affordable prices. In terms of Sun Country Cancellation Policy it allows passengers to cancel their reservations within 24 hours of booking without incurring any cancellation fees.

YOu should check out the FREE professional Chicago Blues Jam at 9pm at the bar: “West on North.” This is a restaurant bar that 20-30 of the best blues players in Chicago show up to and Jam together. INcredably prepared musicians and nothing is practiced. This is led by singer Ya Ya Townsend. Raw, dirty, improvisation with real heart. The most real Chicago blues fun I have had and the cost for entering $0.

I have always wanted to visit Chicago I’m seriously in love with this type of blog as they highlight all of the best things in every city.

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Chicago   Travel Guide

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chicago day trip itinerary

1-day Itinerary in Chicago

  • 1-Day Itinerary
  • All Things To Do
  • 2-Day Itinerary
  • 3-Day Itinerary

chicago day trip itinerary

Art Institute of Chicago Art Institute of Chicago

Home to one of the country's most impressive collections of impressionist and post-impressionist art (plus works from numerous other genres), the expansive Art Institute of Chicago features nearly 300,000 works from all over the world in its permanent collection. You'll find pieces created in the Byzantine era, as well as paintings completed just a few decades ago. Highlights include Jacob Lawrence's "The Wedding," Georgia O'Keeffe's "Sky above Clouds IV" and Grant Wood's "American Gothic." The Art Institute's exhibits also include all sorts of intriguing artifacts, from European armor to the Thorne Miniature Rooms, which showcase interior design and furnishings in Europe and America from the late 13th to early 20th centuries. In addition to the permanent collection, the Art Institute hosts traveling exhibitions covering a variety of subjects and showcasing a diverse array of artists and genres.

The Art Institute of Chicago earns high praise from recent visitors, thanks in part to its impressive collection. Art enthusiasts particularly commend the museum's impressionist collection, which features pieces from famous artists like van Gogh, Monet and Renoir.

chicago day trip itinerary

Millennium Park and Cloud Gate Millennium Park and Cloud Gate free

U.S. News Insider Tip: Construction around the Cloud Gate sculpture will limit the public's access to this top tourist attraction until spring 2024. While you might not be able to snag a selfie with "The Bean," many other attractions are available within the park. – Cortney Fries

A first-time visit to Chicago isn't complete without a stop at Millennium Park. Situated in the Loop just north of the Art Institute of Chicago , this 25-acre space is used to showcase cutting-edge art, architecture and landscaping; it also acts as a backdrop for concerts and festivals. Most visitors come to Millennium Park to see the Crown Fountain and Cloud Gate, better known as "The Bean." Designed by Spanish artist Jaume Plensa, the Crown Fountain features two 50-foot towers that face each other at opposite ends of a shallow reflecting pool. The towers' LED screens project the faces of 1,000 different Chicago residents, which are perfectly aligned with spouts so that it appears they are spitting water on passersby. The water flows mid-spring through mid-fall, while the faces are projected year-round. Cloud Gate – created by British-Indian artist Anish Kapoor – is a 110-ton bean-shaped sculpture forged from stainless steel. The Bean's elliptical shape reflects the Chicago skyline. A quintessential Chicago souvenir is a photo of your reflection in The Bean.

chicago day trip itinerary

Chicago Architecture River Cruise Chicago Architecture River Cruise

A visit to 360 CHICAGO or Skydeck Chicago will give you a good overview of the city's layout. But if you want to learn more about Chicago's sky-high buildings, tag along on an architecture river cruise. During a river cruise, you'll gain great views and historical insight about well-known structures like the Wrigley Building, the Leo Burnett Building and the Fulton House.

Though several companies, including Wendella Sightseeing Co. and Chicago Line Cruises, offer architecture river cruises, most travelers recommend climbing aboard a Chicago's First Lady Cruises boat with a Chicago Architecture Center docent. You'll learn tons of information about the area's architecture, plus catch superb skyline photo-ops.

chicago day trip itinerary

The Magnificent Mile The Magnificent Mile free

U.S. News Insider Tip: The Magnificent Mile, known for its world-class shopping, also has plenty to offer architecture buffs. Book a walking tour with the Chicago Architecture Center and hear the untold stories of North Michigan Avenue's architectural icons. Tours start at $30. – Sarah Estime

For shopping at more than 450 retailers within walking distance in downtown Chicago, make your way to The Magnificent Mile. This portion of Michigan Avenue – which stretches between Lake Shore Drive and the Chicago River – beckons to shopaholics with department stores and luxury retailers like Bloomingdale's, Marcus, Macy's, Tory Burch and Nordstrom. Additionally, The Magnificent Mile is home to several top-notch eateries and luxury hotels, including The Drake , the Sofitel Chicago Magnificent Mile and the InterContinental Chicago Magnificent Mile .

chicago day trip itinerary

360 CHICAGO Observation Deck 360 CHICAGO Observation Deck

One of Chicago's most notable attractions is its skyline, and one of the best places to experience it is at the 360 CHICAGO Observation Deck. Formerly known as the John Hancock Observatory, 360 CHICAGO towers 1,000 feet over The Magnificent Mile from its location on the 94th floor of the John Hancock Center (or 875 North Michigan Avenue as its more formally known). Encased by floor-to-ceiling windows, 360 CHICAGO boasts expansive views of the city; on a clear day, you can see four states. Meanwhile, the interactive screens will help you identify different landmarks that appear in your panorama.

For a different point of view (and an adrenaline rush), test out 360 CHICAGO's TILT. In this mechanized room, visitors hold on to handlebars as the top of the room's windows extend outward, tilting you toward bustling North Michigan Avenue down below. For another memorable way to immerse yourself in the views, try ClouldWalk, a 3D art experience introduced in 2022. Mural artist Nate Baranowski created an optical illusion on the observation deck that makes visitors feel as though they are standing on a crane platform in the clouds.  Should you prefer to experience the view without feeling your heart skip a beat, grab a cup of coffee, a glass of wine or a snack at the cafe and bar, or look for souvenirs in the gift shop.

chicago day trip itinerary

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Phenomenal Globe Travel Blog

The Perfect 1 day In Chicago, Illinois: Itinerary And Travel Guide (2023)

By: Author Irina

Posted on Last updated: October 6, 2023

Categories Blog

The Bean Cloud in Chicago

Oh, what’s that? Did you find yourself in the Windy City for one day during your cross-country crusade of the States? We’ve got good news for you — these might be the most exciting 24 hours ever. From towering skyscrapers to finger-licking deep-dish pizza and live blues performances, Chicago has so many fun things to offer!

After several trips to the city, we came up with a perfect Chicago in one day guide offering a wild mix of corners to explore. Tag along and stroll through historic neighborhoods, try local delicacies, and check out hidden gems along the way. Let’s make this an unforgettable experience together!

Is one day enough for Chicago? Important things to know

One day in Chicago itinerary sounds like a challenging task. Can you soak up all the sights, sounds, and flavors of this iconic American city that fast? Actually, yes! With our guide you’ll be able to go through all the best Chicago experiences in 24 hours! Let’s start with some useful things to know before you go.

Getting in and out of Chicago Airport

A short answer on how to get to and from any of the two Chicago Airports is to, as locals call it, ride the ‘L’ (short for “elevated”). City’s train system will get you downtown for just $5 and with no traffic. Plus, it’s an experience in itself — looking at Chicago’s neighborhoods from the elevated tracks of the nation’s second-busiest rapid transit system after New York’s Subway is a great way to start.

  • CTA Blue Line from/to Chicago O'Hare International Airport (ORD) — operates 24/7, takes 45-60 minutes, costs $5
  • CTA Orange Line from/to Midway International Airport (MDW) — operates from 4 a.m. to 1 a.m., takes 25-30 minutes, costs $5

Luggage storage at Chicago Airport

If spending the night is not on your one day in Chicago itinerary, you might be interested in leaving your luggage at the airport when you arrive. Unfortunately, both city airports don’t have lockers or any storage facilities. So what do you do in this case?

We have a way out for you — Radical Storage , an online service with plenty of secure storage locations. Just follow the link and book a desired drop-off spot. You can choose a location closest to the airport or take a train to the city center with your belongings and leave them at one of the downtown spots. The price for one-bag storage starts at just $5.90/day.

How to get around Chicago in one day

Let’s start with the basics. Chicago is a walkable city. Major tourist attractions in the downtown area are located pretty close to each other, and there are lots of parks and nice pathways perfect for a leisurely stroll. But since you have only one day to spend in Chicago and some of the must-see things are further away from the center, you might be interested to learn about faster (but still budget-friendly) options that don’t include your own two feet.

The cheapest way to get around is, surprise, surprise… public transport. As mentioned before in the article, you can travel fast, save money, and explore the city neighborhoods from above by using the “L” (short for “elevated”) train system. Purchase a Ventra card (single ride: $2.50 for train, $2.25 for bus) and refill it on the go with the app as you need. You’ll also be able to have a free transfer within two hours.

Pro tip: A good idea for a 1-day Chicago itinerary is to buy a 24-hour unlimited pass for just $5 right at the airport.

A perfect day in Chicago — what to do?

In this guide, we offer our take on what to do in Chicago in one day in 2023, unveiling must-see attractions, culinary delights, and local treasures of the city. Without any further ado, let’s embark on this whirlwind of a journey through the heart of the Windy City.

Join an entertaining guided tour

What makes the most sense when you have just one day in Chicago looking for things to do? A sightseeing tour, of course. It’s an exciting and time-saving way to discover the city, especially for those who visit Chicago for the first time. And how about a fun theme excursion that will create lasting memories rather than a typical route through the must-see attractions?

  • One of the things Chicago is known for is its historical ties to organized crime. We took this Gangsters and Ghosts 2-Hour Walking Tour to learn about the city's dark past. This experience proved to be engaging for both history aficionados and those whose knowledge of Al Capone is limited to the 2020 film featuring Tom Hardy.
  • A more family-friendly option of taking a look at the city's brighter side is the 1.5-Hour River Cruise . Discover Chicago's iconic landmarks with ease as you relax on the deck and listen to a live guide.

Take a bite out of Chicago’s Bean

Side note: The plaza housing the Bean is currently undergoing renovations, which means no public access and limited views of the sculpture. Construction is anticipated to continue until spring 2024.

The Bean is what you might want to have for breakfast — only metaphorically, of course, since arriving early allows you to avoid the crowds. In the morning, when the square is nearly deserted, you can capture the best Instagram shots with the skyline views of Chicago reflected from the stainless steel surface of the sculpture.

Once you are done with the “main course”, check out the “side dishes” nearby. Millennium Park (home of the aforementioned Bean) also stations popular tourist attractions like Crown Fountain , an interactive digital art installation with water, and Jay Pritzker Pavilion , an outdoor concert venue known for its innovative design. For a picturesque relaxation spot, consider visiting Lurie Garden .

Pro tip: If you do actually need a cup of coffee and a real snack, pay a visit to Hero Coffee Roasters. We really enjoyed this cozy shop tucked away in a charming alley. Here, you can never go wrong with an order of a classic latte ($4,25) and one of the cafe’s iconic bagels (Sausage, Egg & Cheese for $8,5 is guaranteed to keep you full till lunch).

Discover Chicago’s art gems

Millennium Park in Chicago city

Located pretty close to Millennium Park, the Art Institute makes for an ideal follow-up destination on our one day in Chicago itinerary. It houses a vast collection of paintings, sculptures, and textiles, featuring well-known masterpieces like Grant Wood's “American Gothic”, Edward Hopper’s “Nighthawks”, and Vincent van Gogh's “The Bedroom”. We recommend buying tickets on the website ahead of time, particularly for special exhibitions.

If you are not an art enthusiast, let us offer you a few other notable mentions of Chicago’s most popular museums:

  • The Field Museum boasts the largest, most complete T. Rex skeleton ever discovered (affectionately nicknamed as SUE, after the woman who unearthed it in the 90s), making it a great spot for travelers with kids.
  • Shedd Aquarium , another family-friendly choice, showcases a wide variety of aquatic life.
  • The History Museum is a must-visit for those intrigued by the rich history of Chicago.

Savor the ultimate Chicago deep-dish pizza

After having some food for thought, let’s have some real food. Chicago one day itinerary would be incomplete without a world-renowned pizza. A thick and hearty iconic Chicago-style pie known for its deep, buttery crust, layered structure, and generous toppings is the perfect culinary delight for a hungry traveler.

The top contenders for the title of the best deep-dish pizza in Chicago are the well-known chains, Giordano's and Lou Malnati's . Some locals prefer the former for its signature stuffed pizza with layers of cheese and toppings, while others lean towards the latter for its buttery, flaky crust and chunky tomato sauce. To settle this debate, we suggest you taste both and come up with your own opinion on the matter.

Admire architectural marvels

After having a fulfilling meal, it might be a good idea to get a little exercise. And what's a more enjoyable way to do it than by taking a relaxed stroll and checking out Chicago's wonderful architecture? Many of the most iconic sights of the central area are located within walking distance from each other.

🔸 The Chicago Theater — a legendary lit-up marquee sign is a famous symbol of the city and a go-to spot for awesome photos. 🔸 Marina City — two towers shaped like corn cobs symbolize Chicago's mid-20th-century architecture. 🔸 The Jeweler's Building — according to urban legend, Al Capone used this building with a unique terraced crown as a hideout. 🔸 Carbide & Carbon Building — this fine example of Art Deco is also referred to as champagne bottle building due to its appearance. 🔸 Wrigley Building — a historic building famous for its elegant design and an iconic clock tower. 🔸 The Tribune Tower — a neo-Gothic skyscraper features rocks from global landmarks embedded in its exterior walls.

Take a scenic route

Chicago River

After exploring the architectural wonders mentioned earlier, we recommend using the Chicago Riverwalk as your pathway to the next stop on our 1-day Chicago itinerary. This charming promenade lined with bars and restaurants offers great views along the way. You can get a new perspective on the city's skyline and take some impressive photos.

What’s more, the Riverwalk features riverfront gardens, public art installations, and cozy benches that add to the serene atmosphere and provide ideal relaxation spots. And if you are visiting Chicago in mid-March, you're in for a cool bonus — the chance to witness the green dyeing of the river in celebration of St. Patrick's Day.

Have fun at Navy Pier

Bob Newhart statue

One of the best things to do in Chicago if you only have one day is hanging out at the city's most famous pier. Whether you prefer leisurely walking along Lake Michigan or capturing memories aboard the iconic Centennial Wheel , you're in for a treat with fantastic views!

It’s also a great idea to visit the pier in the evening — the sparkling lights, the cool lake breeze, and the shimmering water combine to create a truly magical experience!

If you're feeling artsy, dive into the Gallery of Stained Glass to admire incredible colored windows. Alternatively, for a day of family fun, the Chicago Children's Museum is a must-visit destination where you and your kids can have a blast.

Soak in Chicago’s skyline

Chicago's Skyline

If you happened to miss out on the breathtaking views from the Navy Pier’s Ferris wheel, we’ve got you covered with this attraction. Welcome to 360 CHICAGO ! Enjoying stunning panoramas from the 94th floor of the John Hancock Building is an essential addition to any one day in Chicago itinerary. General admission starts at $30 but we recommend adding access to a tilting glass lookout for just $9 more.

While in the neighborhood, don’t overlook the Chicago Water Tower . Not only does it showcase exquisite Gothic Revival architecture, but it also serves as a powerful symbol of resilience. The historic water tower is one of the few structures that survived the devastating Great Chicago Fire!

Explore Lincoln Park

What to do in Chicago for a few hours? Lincoln Park will keep you occupied with plenty of engaging activities.

For starters, it offers access to North Avenue Beach with opportunities for summer swimming and water sports. A short stroll away, you'll find Chicago's picturesque waterfront trail — a favorite spot for jogging and biking among locals, as well as a great lookout for gazing at the downtown skyscrapers.

Lincoln Park should also be at the top of your list of the things to do in Chicago this fall. The trees burst into vibrant shades of red, orange, and yellow, creating a picturesque backdrop for your visit. With the summer tourist season winding down, you’ll be able to take a break from the hustle and bustle of the city and relax by one of the beautiful ponds.

Last but not least, the park is home to one of the best things to do for free in the city, Lincoln Park Zoo . If you have one day in Chicago and are in desperate need of activities that will entertain your little ones, this is an ideal destination for exploring a diverse array of animals and beautifully landscaped gardens. Keep in mind though that the zoo closes at 5 p.m.

Chill at Chicago’s best bars

Chicago

You might feel a little tired after a long day. A perfect way to relax and wrap up your 24-hour stopover in Chicago is by immersing yourself in the city's rich musical heritage at renowned venues like Buddy Guy's Legends and the Jazz Showcase .

Not particularly interested in live music and just want to know cool spots in Chicago to grab drinks? Go on a bar crawl through Old Town. The area boasts a wide range of bars, making it a popular choice for nightlife.

If you are willing to experience Chicago's famous speakeasy ambiance during your short stay, the Violet Hour is an ideal destination! It perfectly captures the hidden, Prohibition-era vibe the city is famous for, offering a unique and memorable way to end your visit.

BONUS: Experience city’s unique neighborhoods

If you end up having extra time looking for more things to do in Chicago in 1 day, consider taking the Bloomingdale Trail , also known as the 606.

Once an abandoned rail line that is now a recreational trail and park; it provides a fantastic way to wander through distinctive neighborhoods such as Wicker Park and Logan Square, each boasting its own unique character and charm. It's a great way to delve deeper into the local culture and experience more of what Chicago has to offer in a short time.

What to do in Chicago for a few hours?

Art Institute of Chicago

When you have less than 24 hours in Chicago, making the most of your visit is crucial. Given that a typical ride to the airport takes about 60 minutes, a 6-hour stopover offers a fantastic chance to explore the city's highlights.

Since absorbing all the best landmarks of Chicago is such a time-sensitive mission for you, let us give you a helping hand.

Here are our answers to “What should I not miss at a stopover in Chicago?”

1. Millennium Park: Enjoy the beautiful greenery, admire art installations like Crown Fountain, and take a look at the legendary Bean. 2. Art Institute of Chicago: Pay a brief visit to witness masterpieces like Grant Wood's “American Gothic” and Vincent van Gogh's “The Bedroom”. 3. Chicago Riverwalk: Take a leisurely stroll with scenic views of the Chicago River and architectural wonders like Marina City and The Tribune Tower. 4. Quick Bite: Sample city’s signature foods like a Chicago hot dog at Portillo’s or a slice of deep-dish pizza at Giordano’s. 5. Navy Pier: If you have a little extra time, head to the iconic pier for a Ferris wheel ride and magnificent views of Lake Michigan.

While a short stay like that won't let you see everything Chicago has to offer, it can give you a taste of the city's culture, cuisine, and attractions and a reason to come back!

Where to eat in Chicago?

Food in Chicago

We've figured out what to do in Chicago in one day in 2023, now let’s take a closer look at the best places to eat. The city is renowned for a variety of culinary delights. We’ve already mentioned some great food in Chicago like mouthwatering deep-dish pizza at Giordano’s and Lou Malnati’s or Chicago-style hot dogs at Portillo’s, but here are more of our city favorites:

  • La Josie — an authentic Mexican restaurant in the heart of the trendy West Loop neighborhood. Delicious tacos, creative cocktails, and nice atmosphere.
  • Kanela Breakfast Club — a diverse menu of mouthwatering brunch dishes. Close to major landmarks like Navy Pier and Lincoln Park.
  • Beatrix Market — a grab & go market with a focus on fresh, healthy, and seasonal ingredients. Perfect for a quick lunch.
  • Hero Coffee Bar — high-quality coffee drinks and light snacks to kickstart a perfect day in Chicago.
  • Lockwood Express — try a famous Palmer House brownie in an elegant setting. Plus, savor Bertha's Brownie Latte for an ultimate brownie experience.
  • Intelligentsia Coffee — a range of exceptional coffees in a stylish and welcoming atmosphere. Locations right in the heart of Chicago.
  • Garrett — a chain of gourmet popcorn shops with their signature combo of cheddar and caramel flavors, known as the “Chicago Mix”.
  • Goddess And The Baker — delicious baked goods, from colorful and decadent cakes to fresh pastries and sandwiches.

Where to stay in Chicago?

You have a day in Chicago sorted, it’s time to take care of the night! Unless you plan on partying hard and bar hopping, you’ll need to know what is a good place to stay in the city. Here are our recommendations:

1. Downtown/Loop: Stay in the loop with all Chicago’s main attractions like Millennium Park and the Art Institute right around the corner. You'll discover a range of accommodations to suit various budgets, from luxurious options like 5* The Langham to more economical choices like 3* Central Loop Hotel (from $104/night) — a convenient and affordable base for travelers seeking comfort right in the heart of the city.

2. River North: The area is known for its vibrant nightlife, art galleries, and trendy restaurants and offers a mix of upscale and mid-range hotels. Where to stay in River North? 3* Freehand Chicago (from $99/night) is a blend of private and shared accommodations in a great location.

3. West Loop: A trendy neighborhood known for its dining scene, great bars, and artsy vibe. A great choice for foodies and those seeking upscale accommodations. Where to stay in West Loop? 4* The Hoxton (from $179/night) is a stylish boutique hotel with cozy ambiance, comfortable rooms and a rooftop pool.

Pro tip: Consider spending the night at one of the Sonder apartments. We enjoyed our stay at their South Wabash location , and it was quite budget-friendly, coming in at just around $100/night for 2 people. Our studio was very well-furnished and comfortable.

More tips for visiting Chicago in 2023

River in Chicago

Now that we know how to spend 1 day in Chicago, we would like to share some extra useful tips and answer a few popular questions.

🔹 The best time to visit Chicago is late spring or early fall. The weather is mild, so you can enjoy outdoor activities. Plus, there are fewer crowds than in summer.

🔹 How many days to spend in Chicago? We would say that 2 or 3 days allow you to see all the major landmarks and experience all the fun things at a relaxed pace. But if you don’t have that kind of luxury and your time is very limited, then this guide will help you make the most of your 1-day stopover in Chicago.

🔹 Start your day early to beat the crowds. You will need some fuel to wake up at the crack of dawn: One of the best cups of coffee in Chicago can be found at Hero Coffee Roasters.

🔹 Buy a 24-hour CTA Pass for just $5 to save money on transportation. It gives you unlimited access to the “L” train and bus rides for the day.

🔹 Consider investing in an All-Inclusive Go City Chicago Pass (priced at just $129), which grants you unlimited access to some of the best places to visit in Chicago in 1 day, including Shedd Aquarium, Field Museum, 360 Chicago, Navy Pier Ferris Wheel, and Hop-On Hop-Off Bus. Plan to explore less than 4 attractions? Save money with the Explorer Pass (starting from $87 for 2 choices).

🔹 If you don’t want to puzzle over what can you do in Chicago in 24 hours, you might want to throw caution to the wind and not plan ahead, apart from booking a guided tour for a hassle-free and entertaining experience. Get to know the city with a knowledgeable guide, and then go with the flow: Whatever area you choose to explore in Chicago, it’s bound to have some interesting locations to discover (just steer clear of the South Side, and you’ll be golden). The aforementioned Gangsters and Ghosts 2-Hour Walking Tour and a 1.5-Hour River Cruise are fantastic choices for getting the feelers out on the overall vibe of the Windy City.

🔹 Since we’ve mentioned avoiding particular areas of Chicago (we see you, South Side), don’t think about visiting the iconic Shameless house from the TV show: Not only is it an actual house that is occupied by an ordinary family, but it’s also located in a pretty sketchy Chicago neighborhood. Lip and Fiona won’t come to save your butt from getting jumped in the alleyways, that’s for sure!

🔹 If you get a Chicago-style hot-dog, don’t commit a tourist faux-pas by putting ketchup on the dish. The vendor won’t actually harm you for dousing one of the best hot-dogs in the world with ketchup, but they will judge you pretty harshly.

The perfect one day in Chicago: in conclusion

We hope that with the help of our article you will have the most amazing time in Chicago: Whether you have only a day or a whole week in the Windy City.

Feel free to drop any additional tips or suggestions on what to see in Chicago in one day in the comments below. Your insights and recommendations are greatly appreciated!

The Perfect 3 Days in Chicago Itinerary (2024 Edition)

If you’re planning a long weekend trip to the Windy City and aren’t quite sure what to do, keep reading for our epic 3 days in Chicago itinerary!

While Chicago is the 3rd-largest city in the US, it’s often overlooked by travellers who jet for one of the coasts.

In my opinion, Chicago is the best city in the country. New York and LA are great and all, but I’ll gladly take the friendly Midwestern vibe of Chicago instead.

Situated on Lake Michigan, the Chicago skyline is one of the most beautiful in the world. After all, it was here that the first skyscraper was built in 1885!

There’s so much going on here that you could spend a lifetime there and never run out of things to do.

With a solid Chicago itinerary, you can definitely check out the best of the city in 3 days. Let’s get to it!

Table of Contents

When to Visit Chicago

Chicago citypass, getting around chicago, loop walking tour, chicago hot dog, millennium park, art institute of chicago, willis tower, dinner and drinks, museum campus, riverwalk or river cruise, magnificent mile, chicago deep dish pizza, choose your own adventure, museum of your choice, 360 chicago, lincoln park, best hostel in chicago – hi chicago, best mid-range hotel – congress plaza, best luxury hotel – peninsula, brunch/lunch, how to spend a perfect 3 days in chicago itinerary.

Our 3 days in Chicago itinerary includes:

  • Shedd Aquarium
  • Skydeck Chicago
  • Field Museum
  • Adler Planetarium
  • 360 CHICAGO Observation Deck
  • Navy PierMuseum of Science and Industry
  • Ferris Wheel
  • Crown Fountain

Looking for more awesome things to add to your Chicago itinerary? Be sure to read our guide to the best things to do in Chicago !

3 Days In Chicago Itinerary

Travel Tips for Visiting Chicago

The first step in figuring out what to do during your 3 day Chicago itinerary is planning when you’ll visit.

Winter in Chicago can be painfully cold, which can definitely put a damper on your trip. Unless you enjoy frigid temperatures and cold, biting wind, I recommend skipping out on December-March.

Your best bet is to visit Chicago between May and October. It gets hot and crowded in the summer, but there’s so much going on that it’s worth dealing with those minor inconveniences.

Read Next: Don’t miss out on the best Chicago day trips !

Another huge tip I have before you visit Chicago is to purchase a Chicago CityPASS .

Essentially this is just a multi-use ticket that actually saves you a bunch of money (50% to be precise!) on many great Chicago attractions.

You buy the pass for USD$109, and it includes access to the following:

  • Skydeck Chicago and
  • Adler Planetarium or the Art Institute of Chicago
  • 360 CHICAGO Observation Deck or the Museum of Science and Industry

Best of all, those entrances are mostly express or premium tickets included with the CityPASS , meaning it not only saves you money but saves you time as well.

We highly recommend you pick one up when using our Chicago itinerary to make the most of your time in the city.

Lake Michigan Chicago

Thankfully, getting around Chicago is a breeze thanks to the CTA network of train and bus lines. Chicagoans refer to the train as the “L” because it’s mostly on “el-evated tracks.”

If you’re spending 3 days in Chicago, your best bet is to just pick up an unlimited CTA pass. These cost $20 and are added to a Ventra card.

You can pick up a Ventra card at vending machines for $5 and it’s credited back to your account after you register the card. Read all about getting around Chicago on the CTA website .

You can count on the CTA getting you as far south as the Museum of Science and Industry all the way north to Lincoln Park.

Or consider jumping on and off the open-top bus that will take you all over the city!

In the city center, lots of Chicago attractions are all within walking distance as well.

Now that some of the logistics are taken care of, let’s get this show on the road for your 3 day Chicago itinerary!

Day 1 – Morning

For day 1 of your Chicago itinerary , you’ll need to hit the ground running if you want to maximize your time.

Get a nice early start, crush a substantial breakfast and some coffee, and get ready to rock.

The best way to kick-off your Chicago itinerary is by taking a walking tour of the Loop. This area of downtown is where you’ll find a majority of the sights in Chitown.

You have several options for exploring the Loop. If you enjoy meeting people and getting the insight of a local guide, you can sign up for one of the many options with Free Tours by Foot .

If it’s your first time in Chicago I suggest joining their 10 AM tour of the Loop and Millennium Park. Or if you’re really into architecture, check out their 10:30 Birth of the Skyscraper tour. Both are excellent options!

3 Days In Chicago

Those who prefer a DIY approach can check out the many self-guided tours of Chicago from MetroWalkz. This Architecture/Loop tour makes for a fantastic introduction to the city and is pretty easy to follow.

Whichever option you choose, you’ll get to see some of the most iconic places in the city in just a few short hours. A few of the highlights include the historic start of Route 66, the great Chicago Theatre.

READ NEXT: While you’re exploring the Midwest, be sure to check out the best things to do in Minneapolis, Minnesota !

Day 1 – Afternoon

At this point, the order in which you do things depends on which type of tour you chose. You can be flexible, as it’s a short walk between the next couple of destinations.

Before we move along with the 3 day Chicago itinerary, it’s time for lunch! If you’re down in the Loop and you want to try a local favourite, the choice is easy…

There are countless restaurants to choose from in the Loop, but you don’t want to travel all the way to Chicago to get stuck eating at some overrated chain or overpriced tourist trap.

Al’s is a classic local joint serving up the famous Chicago style hot dogs and their specialty Italian beef sandwiches.

Chicago Hot Dog

One thing to know, a Chicago dog is an all-beef dog on a sesame seed bun. It comes topped with tomato, chopped onions, pickled peppers, relish, a pickle spear, and yellow mustard. Quite simply put, it’s heaven on a bun.

I would be remiss if I didn’t also mention Portillo’s. They also make one of the best Chicago style hot dogs out there.

While they’re a bit out of the way for today’s itinerary, keep them in mind if you’re craving another hot dog during your 3 days in Chicago (and trust me, you will).

Read More: Spending time exploring the Midwest? Be sure to check out our post on all of the best things to do in Kansas City !

Even if you visited on your walking tour, it’s worth it to double back to Millennium Park for further exploration.

Millenium Park Chicago

There’s a lot of cool stuff to see here, including the Crown Fountain and the Cloud Gate.

The latter is commonly referred to as “The Bean” and is one of Chicago’s most popular places to take photos in the city. Don’t forget to snap that quintessential Chicago shot for the ‘gram and keep on moving.

The Bean Chicago

Other Chicago attractions you must see in Millennium Park include the Jay Pritzker Pavilion, the BP Pedestrian Bridge, the Chicago Cultural Center, and the Lurie Garden.

You can easily spend a couple of hours in Millennium Park, especially on a nice day.

Buckingham Fountain and Grant Park are within this same area as well if you want to keep exploring on foot.

While there’s plenty of amazing public art in the Loop, you can’t top the collection at the Art Institute of Chicago. Art lovers will definitely want to include this on their 3 day Chicago itinerary.

Tucked away on Michigan Avenue on the south end of Millennium Park, the Art Institute of Chicago has a seriously impressive collection here and there are always new exhibits featuring modern and contemporary art.

Make the most of your Chicago CityPASS to gain fast entry into the Art Institute of Chicago.

Chicago Art Institute

The museum is open daily from 10:30 AM to 5 PM and stays open until 8 on Thursdays.

Day 1 – Evening

Before the day turns into night, it’s time to hustle over to your next destination of your 3 day Chicago itinerary. Try to time it just right so you make it there about an hour before sunset. Trust me, it’s worth it!

Whether or not you hit the museum, your next stop should be the Willis Tower. This is one of Chicago’s most iconic skyscraper in the city that invented them!

Chicago Skyline

Formerly known as the Sears Tower, this was the tallest building in the world for 25 years. It stands at 442 meters (1,450 feet) tall and is currently the 2nd-tallest building in the US.

If you plan to visit Chicago in 3 days, you definitely need to check the Willis Tower off your to-do list.

Head to the 103rd floor to access the Skydeck Chicago and step out onto “The Ledge” – a glass balcony that lets you look straight down. You’ll want to see views of the city from this spectacular perspective!

Willis Tower

Don’t forget, the best time to go to the Willis Tower is just before sunset. It stays open until 10 PM from March through September and tickets cost $25 for adults and $17 for children.

Once again though, no need to pay extra for a ticket, because the entrance to the Skydeck Chicago is included with your CityPASS .

To celebrate making it through a massive day 1 of the Chicago itinerary, it’s time for dinner and drinks! When it comes to wining and dining, the world really is your oyster in the Loop.

After such a big day, you may want to call it a (somewhat) early night. We’ve still got a lot of ground to cover with this 3 days in Chicago itinerary! Of course, if you want to go out and rage, go for it!

Day 2 – Morning

If you don’t have breakfast included at your hotel, I highly advise you to start day two off at Yolk’s South Loop location.

This is the perfect spot to load up with a big breakfast and coffee before another big day in the city. Go ahead and carb up – there’s going to be a lot of walking today!

After breakfast, walk across the street to check out Agora – a sculpture composed of 106 headless figures.

Keep walking east towards Lake Michigan to reach the Museum Campus. Here you’ll find the Field Museum, Shedd Aquarium, and the Adler Planetarium.

With just 3 days in Chicago, you’ll probably want to just visit one. Having been to all three, I’ll cast my vote for the Field Museum.

Chicago Field Museum

There are so many cool exhibits at the Field Museum and they’re always changing.

At the moment, they have: Inside Ancient Egypt, Bird’s of America, and Brewing Up Chicago, among others. Check their website to see what’s going on before you visit.

Tickets for the Field Museum cost $26 for adults and $19 for children for basic admission.

If you got the CityPASS, your admission is included in all three, unless you hit the Art Institute on day one. If you’ve got the pass, you might as well hit the aquarium as well.

Shedd Aquarium

To be honest, the aquarium is pretty sweet. Even if you don’t have the CityPASS, you should probably try to squeeze it in.

Tickets are $40 for adults and $30 for kids and you’ll definitely get your money’s worth.

Day 2 – Afternoon

There are a few cafes and food stands around the museum campus, so go ahead and grab a snack and a drink before powering on.

This is one of those days where it’s best to have a big breakfast and dinner and just graze during the day. When you’re trying to cross off so many things to do in Chicago in 3 days, you gotta keep moving!

The museum campus is the southern part of Grant Park. Known as “Chicago’s Front Yard,” this massive green space is to Chicago what Central Park is to NYC.

Take a stroll through the park to see such landmarks as the Buckingham Fountain, the Rose Garden, and the Seated Lincoln Statue. There are plenty of benches if you need to sit down and chill for a bit.

Grant Park Chicago

Grant Park also hosts some of the biggest events in the city, such as the Taste of Chicago and Lollapalooza.

Some are free and others cost hundreds of dollars, so be sure to check the calendar of events to see what’s happening before you book your trip.

Hug the coast and keep walking north along the Lake Michigan until you reach the Riverwalk. This scenic pedestrian path along the Chicago River is the perfect place for a leisurely stroll.

If your feet are feeling a bit tired from all the walking, you can enjoy the spectacular Chicago architecture on this fantastic river cruise instead .

Taking in the sights along the Chicago River is definitely one of the top things to do in a 3 day Chicago itinerary.

Chicago River

Wendella Boats has an architecture river cruise that comes highly recommended. Make sure you have your camera for this one, as you’ll get some epic views of the city.

Day 2 – Evening

I’m sure you’re ready to eat your hand by now, but you’ve just got to soldier on for a bit longer. Trust me, it’s going to be worth the wait!

On the other side of the Chicago River, you’ll find the Magnificent Mile, a short stretch of Michigan Avenue in downtown Chicago. This is the city’s premier commercial district, full of high-end shops, nice restaurants, and boutique hotels.

Along the Magnificent Mile, you’ll also see several historic skyscrapers, such as the Wrigley Building, Tribune Tower, and the Old Watertower.

The latter is home to the City Gallery, which has Chicago-focused photography exhibits. It’s totally free to visit, so you may as well check out while you’re in the area.

Even if you’re not doing any shopping, it’s worth a quick stroll along the famous Michigan Avenue. That’s because it’s leading you to…

You had the hot dog on day one, so it’s time to dig into some Chicago-style deep dish pizza.

Since it’s cooked in such a deep pan, a Chicago-style deep dish pizza can be stuffed with mountains of cheese. Of course, you can add whatever other toppings you like as well.

Now you see why I’ve been torturing you by making you walk around all day waiting for dinner! This deep dish pizza is seriously delicious and filling, so I wanted to make sure you could at least have a few slices.

Chicago Pizza

There are plenty of places cooking up Chicago-style deep dish pizza, but I brought you here because two of the best are easily accessible.

Get to the corner of Michigan and Superior and you have an important choice to make. Take a left and you’ll go to Giordano’s. Hook a right and you’ll be at Gino’s East.

Just go ahead and flip a coin because you win either way. Both places are legendary for their deep dish pizzas, so you really can’t go wrong.

Not far from the Magnificent Mile, you’ll find Navy Pier. If you’re spending 3 days in Chicago on a long weekend, this is the perfect place to be on a Saturday night.

First up, you can take a ride on the Centennial Ferris Wheel. Tickets cost $18 for adults and $16 for children, but you can save a few bucks if you book online .

Navy Pier Chicago

From the end of May until the end of August, Navy Pier also hosts bi-weekly fireworks shows. These happen on Wednesdays at 9:30 PM and Saturdays at 10:15.

To take in the spectacle, you can find a spot to stand on the Navy Pier or sign up for an evening cruise. Enjoying the fireworks as you cruise around is a great addition to your Chicago itinerary.

If you have any gas left in the tank after all of the activities at the Navy Pier, congratulations! I just ran you ragged all over Chicago on day two. That’s why it’s time to choose your own adventure!

For many, that will probably involve grabbing a casual drink from the hotel bar and getting some sleep. That’s totally fine. I’m getting to the age where that sounds like a perfect Saturday night!

For the young whipper-snappers among us, you’re probably itching to enjoy a big night out on the town. Go for it, you crazy kids!

Your options are endless. There’s live music of all varieties, comedy clubs, and just about every type of bar under the sun.

Whether you’re looking for a speakeasy that whips up creative cocktails, a classy wine & jazz joint, or just a good ole’ fashioned dive, you can find it in Chicago.

Tiki Bar Chicago

In this part of the city, one of my personal favourites is Three Dots & a Dash. This awesome tiki bar has an impressive selection of cocktails that will transport you to the Caribbean in no time.

If you’re going to go hard one night, this is the one to do it! Bars in Chicago typically close at 2 AM, but there are several that stay open as late as 4 on the weekend. You’ve been warned…

Day 3 – Morning

How early the last day of your 3 day Chicago itinerary starts depends entirely on how late your night went!

Those who already regret ordering that last round may need to sleep in a bit and smash a greasy brunch, while the go-getter set who actually slept will be up and at them. Life is all about choices, people!

Whatever you did the night before, get some food and caffeine in your system and get out there to wind down this 3 day Chicago itinerary.

Our third and final day in Chicago starts off with a leisurely museum visit. Within a few blocks of each other, you can take your pick between three excellent museums.

Art enthusiasts will gravitate towards the Museum of Contemporary Art, which highlights post-WWII art.

Those more interested in architecture and antiques may want to hit the Richard H. Driehaus Museum. It’s in a restored 19th-century mansion and brings you right back to the Gilded Age.

Chicago is very much a sports city, as people here are very passionate about their teams. Check out the Chicago Sports Museum, which is full of memorabilia and plenty of fun exhibits.

I know I already sent you to the Willis Tower on day one, but it’s still worth a trip to John Hancock’s 360 Chicago on Michigan Avenue.

This observation deck on the 94th floor of the John Hancock Building provides a whole different perspective on the city that you will definitely want to see.

Chicago Parks

Plus, if you bought a CityPASS your admission to the John Hancock building is already included! If you didn’t grab the pass, a ticket is $25 for adults or $15 for children.

Those who are feeling adventurous (and not hungover) may want to take a ride on Tilt – Chicago’s highest thrill ride.

If you need some hair of the dog instead, you can grab a ticket that includes your choice of adult beverage. Sunday Funday!

If you don’t purchase the Chicago CityPASS consider purchasing this ticket to enjoy the views from the 94th floor of the John Hancock building’s 360 Chicago.

Day 3 – Afternoon

Once you come down from 360 Chicago in John Hancock building, you have plenty of options for lunch. Within a few blocks, you can find Cuban, Vietnamese, Mediterranean, and the Chicago staple of deep dish pizza.

If you want a lunch with a view, consider eating at The Kennison. This upscale bar and restaurant offers sweeping views of Lincoln Park. The menu is modern American and they have lots of amazing cocktails and drinks.

Hop on the bus, order an Uber, or walk 30 minutes to our next destination – Lincoln Park.

There’s a lot to do in this huge park on the shores of Lake Michigan. North Avenue Beach is at the south end.

Chicago Beach

On a beautiful day in Chicago, it’s hard to beat lounging on the beach and swimming in the lake. You can also play some beach volleyball and rent a SUP or bike if you want some more activity.

In the middle is the Lincoln Park Zoo, which is totally free to visit. Sightseeing gets expensive, so this awesome free attraction is definitely one of the top things for any Chicago itinerary.

Lincoln Park Zoo

After such an action-packed 3 days in Chicago, you should definitely just take it easy and enjoy all that Lincoln Park has to offer. You’ve covered some serious ground in a short time, so congrats on that!

Day 3 – Evening

At this point in the journey, you have absolutely crushed 3 perfect days in Chicago. Order a celebratory drink or two and enjoy your last evening in the city!

What you choose to do with your final night all depends on when you’re visiting and what your interests are. That’s why it’s time once again to…

In a perfect world, the Cubs would be playing a night game while you are visiting Chicago. You could head north to Wrigley Field and enjoy America’s pastime at the 2nd-oldest ballpark in the country.

The Cubs play about 80 home games between April and September, so there’s a good chance they’ll be in town when you are. Even if you’re not a baseball fan, I recommend hitting a game if at all possible.

Wrigley Field

Chicago actually has two MLB teams. But the White Sox ballpark is way south of where you’ll be on day three and not worth the trip if you ask me.

If you’re making a trip to Chicago between October and April, you may be able to catch the Bulls (NBA), Blackhawks (NHL), or the Bears play a home game. Check their schedules to see what’s going on when you’re in town.

Those who prefer a good laugh can head back to the south end of Lincoln Park. Just a block away, you’ll find three of the city’s best comedy clubs – Second City, UP, and Zanies.

I pretty much always travel to Chicago for live music, so you know I’m going to toss that in here!

The city has an epic music scene and there’s always something playing here. Whether you’re into rock, hip-hop, jazz, electronic, blues, pop, or whatever it is you wacky Millenials listen to these days, there’s a show for you.

I usually check Jambase to see what shows are playing.

Congratulations, my friend. You made it through an insane 3 days in Chicago itinerary and experienced the best that the Windy City has to offer.

I’d say that calls for a toast! If you want to finish up with a true Chicago experience, order a shot of malort. This infamous Chicago liquor is pretty hard to describe, so I’ll let its label do the work:

“ Malort has the aroma and full-bodied flavor of an unusual botanical. Its bitter taste is savored by two-fisted drinkers .”

I’m not going to sugar coat it – this stuff is awful. It’s a rite of passage here in Chicago, though. Eat the hot dog. Drink the malort. Praise be to Ditka. You’re now a little bit Chicagoan.

After you finish that putrid shot of malort, switch to a delicious Chicago craft beer. There are plenty of choices here, including Lagunitas, Revolution, and Goose Island.

Chicago Bars

I hope you enjoyed this massive tour of Chicago!

From Navy Pier, to Millennium Park, the Chicago riverwalk, the famous Chicago hot dogs and more, visiting Chicago is never dull.

Hopefully this 3 day Chicago itinerary has been inspiring and gives you an idea of what to do in the Windy City.

Chicago Itinerary Travel Guide

Now that you know what to do with a long weekend in Chicago, I’ve gone ahead and put together a mini-guide to this awesome city to help you decide where to stay, where to eat, and of course where to drink!

Where to Stay in Chicago

You’re probably wondering where to stay, especially if it is your first time in Chicago.

Most first-time visitors choose to base themselves in downtown Chicago, and for good reason. Here are countless options for accommodation, sightseeing, dining, and nightlife.

As you might expect, staying downtown comes with a price tag. Other popular places to stay that are a bit cheaper include River North, Lincoln Park, Bucktown, and Wicker Park.

When it comes to places to lay your head, Chicago has it all. The city has 5-star luxury hotels, quaint B&Bs, dingy motels, fun hostels, and plenty of options on sites like Airbnb.

Here are a few options to suit all budgets:

Hostelling International is a trusted name in backpacker accommodation, and their downtown Chicago location is definitely the best hostel for visiting Chicago.

They have several different options for both private and dorm rooms. You can get a bunk for under $40 a night here – a steal for this fantastic location.This includes a free breakfast, and they also have free walking tours during the day and free activities at night.

That’s not all, though. They’ve also got a huge lounge with a ping pong table and a TV room with plenty of movies. Best of all, this hostel is environmentally-friendly. They have reusable products in the kitchen and recycling points all around the building.

This historic downtown Chicago hotel dates all the way back to 1893. Don’t worry – it’s had several updates over the years!

You really can’t beat the location of this place. I usually stay with friends in more residential neighbourhoods, but this is my go-to spot when I want to be in the middle of all the action.

From here, you’re just across the street from Grant Park. Many of the rooms here even boast a nice view of Lake Michigan. With rooms starting as low as $115 a night, it’s a pretty awesome deal staying here.

The 5-star Peninsula Chicago was recently named the 2nd best hotel in the country by US News & World Report. This place is fancy, people!

It’s located right on the Magnificent Mile, so it’s surrounded by high-end shops. This is definitely where the fabulous people stay.

In addition to the super swanky rooms, you can enjoy the hotel’s three different restaurants and its impressive fitness centre.

Taking up the top two floors of the building, it features a 25-meter pool and an award-winning spa. Rooms start at around $600 a night here.

Where to Eat and Drink in Chicago

I’m very fortunate to have a good friend who is heavily involved in the hospitality scene in Chicago.

I reached out to him to get a list to add to this guide. He’s never done me wrong with food & drink recommendations, so you can take these to the bank the next time you visit Chicago!

  • Dove’s Luncheonette
  • Joe’s Stone Crab: It’s a steakhouse and it’s hard to get into at night, but if you go for boozy brunch it’s great.
  • Parson’s Chicken & Fish: Not really brunch but just a great people-watching patio.
  • Big Star: Chicago classic taco joint with highly sought after patio
  • 3 Arts Club

Best Chicago Restaurants

  • Bavette’s Bar & Boeuf
  • The Roister
  • Green Street Smoked Meats: A great BBQ joint and High Five Ramen is below.
  • Maple & Ash
  • Nico Osteri
  • Billy Sunday
  • Aviary (try to get down to the office)
  • Violet Hour
  • Start at Scofflaw and work your way over to Best Intentions
  • Longman & Eagle 
  • The California Clipper: Been around since before prohibition!

DISCLAIMER: Some of the links in this article are affiliate links, which means if you book accommodation, tours or buy a product, we will receive a small commission at no extra cost to you. These commissions help us keep creating more free travel content to help people plan their holidays and adventures. We only recommend the best accommodations, tours and products that ourselves or our fantastic editorial team have personally experienced, and regularly review these. Thanks for your support, kind friend!

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About the Author - Sasha and Rachel

One of our official NOMADasaurus team writers, Sasha and Rachel, otherwise known as the Grateful Gypsies, are a world travelling, English-teaching, jamband-following couple passionate about travel, culture, and music. From working in Beijing to studying in Bali to traversing the USA on Phish tour, you can follow them on their long, strange tour at Grateful Gypsies .

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3 thoughts on “The Perfect 3 Days in Chicago Itinerary (2024 Edition)”

I would love to visit Chicago in 2024! This itinerary looks perfect!

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Many thanks for your superb article about 3 days in Chicago.

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In One Day in Chicago

The day begins with a walking tour of the Loop , which is the best way to get your bearings (and understand why Chicago's architecture is world-famous). Then you can squeeze in a quick visit to one of the city's preeminent museums before strolling along Michigan Avenue, Chicago's most famous thoroughfare, which takes you to the ritzy Gold Coast neighborhood. If possible, follow this itinerary on a weekday, when downtown offices are open and the sidewalks buzz with energy. This route works fine on weekends as well, but you won't experience quite the same big-city rush.

Start: Green, Orange, Brown, or Purple lines to Adams, or Red Line to Jackson.

1. Chicago Architecture Center Start your day with the Chicago Architecture Center's "A Walk Through Time" tour, which begins at 11:30am on certain days of the week (2pm on others; check website for details). The 90-minute walking tour takes you to the oldest high-rises in the Loop, and the docents explain why these early office buildings were revolutionary. Sure, you'll get a basic architecture education, but this is also a great way to get a sense of the Loop's layout and dramatic canyonlike vistas. Another popular tour is "Modern Skyscrapers."

2. The Art Institute   Even if you are hard-pressed for time, make sure to at least stop in to view the Impressionist collection on the second floor, a highlight of Chicago’s grande dame of museums. With 33 paintings by Claude Monet, dancers by Degas, and Seurat’s legendary A Sunday Afternoon on the Island of La Grande Jatte , this museum is a must for art lovers.

3. Millennium Park

With its up-close-and-personal skyline views, this sprawling greenspace is universally loved for its gorgeous landscaping, classically inspired architecture, and public entertainment spaces.

If the weather is fine, Millennium Park is an ideal spot for a picnic lunch, which you can buy at the Park Grill & Cafe (11 N. Michigan Ave.; tel. 312/521-7275). The Crown Fountain, and its two towers of glass blocks with a shallow reflecting pool between them, is the place for kids to splash around in warm weather (late at night, you’ll find revelers doing the same). Faces of Chicagoans are projected through the glass—and their mouths spew water when you least expect it. A tourist rite of passage is having a photo taken in the reflection of “The Bean,” (officially Cloud Gate ), which is Chicagoans’ unofficial favorite sculpture, made of highly polished steel that reflects the nearby skyline, landscape, and lights. For the most mind-bending funhouse view, stand underneath the sculpture. The park’s centerpiece is the Jay Pritzker Pavilion, an outdoor music venue designed by Frank Gehry and host to the nation’s only free, outdoor, municipally supported classical music series, the Grant Park Music Festival; massive stainless steel ribbons top the stage. Another Gehry-designed standout, BP Pedestrian Bridge, curves and winds its way over Columbus Drive to Maggie Daley Park.  This may well be the park to end all parks, with an elaborate playground, mini golf, tennis courts, a climbing wall, and, in the winter, a skating ribbon. Finally, stroll The Lurie Garden, where 250 varieties of native perennial plants re-create a Midwestern prairie.

4. Park Grill In the winter, this restaurant overlooks Millennium Park's ice-skating rink; come summer, the rink transforms into an outdoor cafe, perfect for sipping a drink and admiring the skyline. Stay for a full meal or grab a sandwich to go.

5. Michigan Avenue Bridge Walk north along Michigan Avenue to the Chicago River, where you can gaze up at the Gothic splendor of the Tribune Tower and the white brilliance of the Wrigley Building from Chicago’s most famous bridge, dating back to 1920. Views from every direction are stunning, but for one of the city’s best photo ops, look west down the river. 

6. The Magnificent Mile The 14-block stretch of Michigan Avenue from the river to Oak Street, known as the "Magnificent Mile," is shopping central, a dense concentration of high-rise malls, designer boutiques, and practically every mass-market clothing brand. Even if you're not a shopper, it's worth a stroll; busy at almost all hours, it's great for people-watching. Some Chicagoans dismiss the Mag Mile as too touristy, but I think walking here makes you feel like you're part of a vibrant metropolis.

7. 360 Chicago 875 N. Michigan (formerly the John Hancock Center) may only be Chicago's third-tallest building, but the view from the top is spectacular: In the right weather conditions, you can see all the way to three other states (Wisconsin, Indiana, and Michigan). The "talking telescopes" help you get your bearings by pointing out landmarks in each direction.

8. Oak Street Beach Where Michigan Avenue merges into Lake Shore Drive at Oak Street, head down the underpass to get to Oak Street Beach, a curved stretch of sand that's a summertime hotspot and a great background for photos. Bikers, skaters, and joggers fill the paths, while kids play in the sand. Think of it as Chicago's own miniresort getaway — just don't plan on swimming in the frigid water.

9. 3rd Coast If you're tired of generic chain coffeehouses (of which Chicago has plenty), stop by this somewhat shabby lower-level cafe that welcomes both well-heeled locals and the occasional starving artist. In addition to the usual lattes and muffins, there's a full lunch and dinner menu, and wine and beer are available.

10. The Gold Coast To get an idea of how Chicago's wealthiest live, take a stroll through this neighborhood of historic town homes (including the original Playboy Mansion, at 1340 N. State Pkwy.). The tranquil, tree-lined streets are only a few blocks away from Michigan Avenue, but they feel like a different city. Finish up the night with dinner at one of the many restaurants in River North, or catch a show and discover Chicago's vibrant theater scene .

Note : This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.

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View of Chicago skyline from above with Lake Michigan visible to the right

3 Days in Chicago: The Ultimate Weekend in Chicago Itinerary

Chicago is a vibrant city that feels very alive, and with the perfect 3 days in Chicago itinerary, it’s possible to sample the best of the city over a long weekend!

The city is always on the move, and there isn’t an hour in the day that you won’t find at least 10 unique and adventurous things going on around town.

Music and food festivals pull out all the stops in Chicago, on top of the arts and cultural events that dot the city throughout the year.

Are you into food and drinks, lake views, and most of all, fun? Then Chicago is the place to be. There is enough here to explore for months, and we are going to pack all of the best events and activities into a 3 day long weekend itinerary to experience the essence of Chicago. 

Note: this Chicago blog post was written for Our Escape Clause by former Chicago locals Zach & Julie Ruhl, the travel couple behind Ruhls of the Road . Thanks for joining us, guys!

Table of Contents

Day 1 in Chicago Itinerary: The Bean, Skydeck & Great Chicago Food

Day 2 in chicago itinerary: lincoln park, wrigley field & beyond, day 3 in chicago itinerary: magnificent mile, navy pier & an afternoon adventure, where to stay for 3 days in chicago, where to eat during your chicago weekend getaway, getting around during 3 days in chicago, when to spend a long weekend in chicago.

Zach and Julie Ruhl of Ruhls of the Road dancing in a Chicago Park. They are the authors of this 3 days in Chicago itinerary

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Chicago is an enormous place. The city covers miles in each direction, with awesome things to do located all over the map. Therefore, this Chicago itinerary is going to thoughtfully take you from place to place, minimizing travel time and maximizing adventure.

Your first day in any new city should no doubt include some of the most signature sightseeing highlights there–and this Chicago itinerary is no exception, starting with a popular activity that is relatively new in Chicago: the Riverwalk. The current version of the Riverwalk was completed in 2017 and is an excellent place to start your Chicago weekend getaway.

Start your weekend in Chicago with a walk on the Chicago Riverwalk.

The Chicago Riverwalk starts at Wolf Point, near where the Chicago River turns from East/West to North/South. From there, the Riverwalk continues for over a mile, to the point where the Chicago River meets Lake Michigan.

Along this beautiful walk, you’ll pass a few awesome cafes and restaurants. This is a great place for a morning coffee, watching the morning hustle and bustle of America’s third-largest city. On top of that, the morning walk counts as your exercise for the day!

If you fall in love with the Riverwalk, then come back for a happy hour one evening. Riverside wineries and bars open up during the evening, complete with sets of outdoor games, live music, and some great entertainment! 

Photo of Chicago Riverwalk near a bridge that crosses the river, a great way to kick off your 3 days in Chicago itinerary

Check out Millennium Park.

At the end of the Chicago Riverwalk, you’ll reach Lake Michigan. Turn right here and head South to Millenium Park, where you’ll find an excellent location for soaking in the Chicago skyline from a beautiful park in the huge city center.

Millennium Park is an awesome Chicago sightseeing destination for two reasons. First off, it is just a great park full of fun things to do in Chicago !

There is an awesome playground for kids to play on, a great dog park for your four-legged friends, a huge green space to sprawl out for a picnic, a live music amphitheater, the Crown Fountain with a reflecting pool, endless gardens, and so much more!

You could spend a whole day at Millenium Park and not grow bored.

The second reason Millenium Park is so great is its proximity to everything. The park is great, but what makes it so impressive is that you are literally in a natural oasis amidst the concrete jungle of downtown Chicago.

Look around you while in the park, and you’ll see the towering structures of the Willis Tower, the Aon Center, and the rest of the enormous Chicago skyline.

Zach and Julie Ruhl at Millenium Park in Chicago Il, they are the authors of this long weekend in Chicago itinerary

Snap photos at The Bean.

At the edge of Millenium Park is The Bean, AKA Cloud Gate, Chicago’s most photographed (unofficial) monument.

The Bean is a huge monument, standing over 30 feet tall and 60 feet long, that is made of polished chrome and has no visible seams. This structure is truly unique and is an awesome downtown Chicago sight. 

The Bean is perfectly reflective, and due to its shape, the reflections can make for very fun images. It is essentially a gigantic magic mirror, placed in the middle of a bustling downtown environment.

Spend some time enjoying the fun reflections you can see as you walk in a circle around and under The Bean, then head for some food.

Downtown Chicago should have plenty of options on your way to your next stop: the Willis Tower. 

Chicago bean in Millenium Park at blue hour

Admire views of Chicago from the Willis Tower Skydeck.

The Willis Tower is Chicago’s tallest building and the second tallest in the United States. At one point, this skyscraper was even the tallest building in the whole world, and held that title for 25 years! There’s no doubt that this is a must-see spot on any 3 day Chicago itinerary.

When you visit the Willis Tower, there are really two things you need to do. First off, admire the size of this monstrosity from below. The building literally reaches into the sky, and from the bottom seems impossibly huge. Walk around it marveling upwards, just make sure to lose your attention and wander into the city streets!

The other way to see the Willis Tower is, of course, from the top. The Skydeck is at the very top of the building, where you can see Chicago stretch beneath you for miles and miles in each direction into the horizon.

If you have the stomach for it, there is even a glass-bottomed section where you can literally step out into the sky, or at least it looks that way. From the glass floor, you can see down over 1,000 feet to the streets beneath you. This is quite an incredible experience and one that you won’t get anywhere else in the United States!

Book your Skydeck tickets for the Willis Tower today!

View of Chicago IL skyline from willis tower skydeck, a must-see during a 3 day Chicago vacation

Finish your first day in Chicago in West Loop on Randolph.

The West Loop is an up-and-coming neighborhood in Chicago. This area seemingly has a great new restaurant pop up each week and has some of the most delicious food and one of the most fun atmospheres in the city.

Randolph Street in the West Loop is the culinary center of the neighborhood and is where you should head for dinner and drinks on your first day in Chicago. If you have the time and energy, the very best activity is to have a drink at a few different places, hopping from place to place and soaking up as much of this wonderful neighborhood as you can.

Each restaurant will have a unique vibe and atmosphere, so keep hopping around until you find the one you love best.

Want to make sure you experience the best food in the neighborhood? Add this popular West Loop Food Tour to your Chicago itinerary!

Macy Clock on Randolph and Street Street in Chicago Illinois

Close out your first night in Chicago at an Irish pub.

Chicago has a huge Irish population, and therefore quite a few Irish pubs located around the city. Our best recommendation is to find one close to your hotel and pop in for a Guinness as a night-cap. Enjoy the Chicago atmosphere, and then head to your hotel to get some sleep before heading off on your second day’s worth of fun things to do in Chicago!

Day 2 in Chicago is going to be a day full of exploring Chicago’s famous North Side. The North Side is awash with classic Chicago food options (Chicago loves its food…) as well as awesome sites to see and things to do. First up is the famous Lincoln Park.

Start the day with a stroll through Lincoln Park.

Lincoln Park is a huge and sprawling greenspace alongside Lake Michigan for 7 long miles. This is, in fact, the largest park in all of Chicago! And it also may very well be the most beautiful.

Alongside Lake Michigan, Lincoln Park has a few different beaches, as well as seemingly endless biking and walking trails. If you would rather bike than walk, then there are many bike rental options scattered all around the park, and around Chicago as a whole.

While strolling or biking through Lincoln Park, make sure to stop and see the Belmont Rocks, North Pond, and the Signal of Peace Monument. Along the way, admire the natural beauty and enjoy the sounds of birds singing as you bring on your second day in Chicago.

Chicago skyline as seen from Lincoln Park, one of the best places to visit in Chicago IL on a weekend in Chicago vacation

Soak up the sun at North Avenue Beach.

North Avenue Beach is one of Chicago’s largest and most popular beaches. Located right alongside Lake Michigan, this vast expanse of white sand makes for a great place to enjoy the beautiful Chicago summer sun.

If you are traveling with a group, then there are opportunities for some beach volleyball at North Avenue Beach! At the beach, you can rent a net and a ball (rentals are by the hour) and play some volleyball on the sand in view of the Chicago skyline!

While at North Avenue Beach, you must make a stop at the famous beach house that is shaped like a boat. This is also the location of Castaways, a bar and grill on the roof of the beach house serving yummy drinks with an incredible view. 

Head to Wrigley Field & Wrigleyville.

You can’t visit the North Side of Chicago and not see Wrigley Field. As one of the most famous baseball stadiums in existence, and the home of the Chicago Cubs, this is a must-see stadium, especially for sports fans.

Wrigley Field is located right in the heart of Wrigleyville on the North Side. Surrounded by residential areas and a huge bar and restaurant scene, this area is a magnet for good times, especially when the hometown Cubs are lacing up their cleats for a game.

If you are fortunate enough to be in Chicago while the Cubs are playing, head to Wrigley just for the experience of people watching and cheering on the hometown team. If you’d like, you could even try and buy some tickets, and usually, you can get a good deal on seats if you are okay purchasing them after the game is already in the 2nd or 3rd inning.

Wrigleyville, the neighborhood surrounding Wrigley Field, is an excellent place to hang out, have a drink, and hop around a few of the local establishments. Each of them has a great atmosphere, delicious, food, and of course a wide array of beers on tap.

Wrigley Field scoreboard in Chicago Illinois

Sample some Malort.

Malort is a Chicago specialty liquor and is something anyone over 21 should try when they visit the Windy City.

The liquor itself is not good because of taste, in fact, it tastes pretty bitter, and most people find it awful. However, it is all about the experience of trying something the locals love! If you’d like to experience the local culture of Chicago, then you have to try Malort at least once.

Finish the Day at the John Hancock Center Signature Lounge.

The John Hancock Center is the best building in Chicago. That may be a controversial opinion, but it is so true. The enormous slanted walls of the Hancock reach over 1,000 feet into the Chicago sky, with huge beams in a crisscrossing X pattern the entire way up. The building is an architectural masterpiece and is a wonder to see from the base.

The best place to experience the Hancock Center, however, is not from the base. It is from the Signature Room.

What is the Signature Room? It is an incredible 95th-floor bar and restaurant with an absolutely stunning view of Chicago. The Signature Room offers a 360-degree view of Chicago from above and is especially breathtaking as the sun sets and the sea of lights emerges beneath you.

Experiencing an evening at the Signature Room is a wonderful experience, and will be a highlight of your visit to Chicago. If you are visiting on a budget, just order a drink here, as dinner can be expensive!

Chicago Skyline at sunset--views like this are plentiful throughout this 3 day Chicago itinerary!

Day 3 is going to be spent exploring more awesome sites and destinations in downtown Chicago. It is going to be a day where you can see as much as you want, and take it all in at your own pace. Choose your own adventure and make today special as you finish up your long weekend in Chicago!

Walk down the Magnificent Mile.

Start the day with a trip down the Magnificent Mile. This is a section of Michigan Avenue that is the retail center of Chicago. The street is lined on both sides with tons and tons of flagship stores, boutiques, and shopping malls.

Along the Magnificent Mile, in addition to all of the premier shopping, there are a few awesome sights you’ll see during this part of your Chicago weekend getaway.

The Wrigley Building is an awesome structure located right where Michigan Avenue meets the Chicago River. The Tribune Tower and the Chicago Water Tower are also wonderful landmarks along this stretch.

Office buildings along Michigan Avenue in Chicago Illinois--don't miss a chance to walk down the Magnificent Mile during your 3 days in Chicago sightseeing trip

Explore Navy Pier.

Just a few blocks from the Magnificent Mile is Navy Pier, an absolute must-visit destination on any Chicago visit. The Navy Pier is, as the name suggests, a large pier, formerly used by the Navy, that extends straight out into Lake Michigan. 

These days, Navy Pier is an awesome destination that is used for a wide variety of attractions. First off, there is almost always some form of live entertainment or shows that are happening over a weekend at Navy Pier. On top of that, the pier is lined with awesome bars and restaurants, as well as shops and boutiques.

The view from the end of Navy Pier is excellent. First off, you’ll get to see the vast expanse of Lake Michigan on 3 sides of the pier. However, when you look back at the city, you’ll get a view of the full skyline including the Willis Tower and the Hancock Center. Do you want an even better view? Because there is one way to get it… There is a HUGE Ferris wheel that you can ride to get a stupendous view of the entire Chicago skyline and Lake Michigan!

Chicago Navy Pier with skyscrapers visible in the background and Lake Michigan in the foreground

Visit Buckingham Fountain in Grant Park.

After exploring Navy Pier, head to Grant Park, another of Chicago’s excellent downtown parks. Here you’ll have the chance to explore a huge area of green space, complete with monuments, statues, and a great lakeside walkway. At the heart of Grant Park, you’ll see Chicago’s most famous and beautiful fountain: Buckingham Fountain

Buckingham Fountain is at the center of Grant Park and is a great place to sit and enjoy a coffee or picnic. The fountain itself is beautiful, but it is made even better by the great Chicago skyline in front of you, and Lake Michigan behind.

Close up of Buckingham Fountain in Grant Park in Chicago Illinois

Further South in Grant Park you’ll find three other excellent Chicago sightseeing spots to consider adding to your 3 day Chicago itinerary:

Field Museum, Shedd Aquarium + Adler Planetarium

On the south side of Grant Park are 3 beautiful buildings, each of which houses an awesome adventure. The Field Museum is one of the largest natural history museums in the world and is home to some of the best exhibits you can possibly imagine. When we visited in the past, the dinosaur exhibit left us astounded, as they had a full-size Tyrannosaurus Rex named Sue!

The Shedd Aquarium is a world-class aquarium located just east of the Field Museum on Lake Michigan. This aquarium is stunning both from the outside and inside and offers hours of exploration as you make your way through the grounds.

Finally, the Adler Planetarium, America’s FIRST planetarium, is a wonderful place. This place offers the chance to explore things that are out of this world, literally. If you are at all interested in space, astronomy, or astrophysics, then you will have the time of your life at the Adler Planetarium.

Exterior of Field Museum in Chicago Il as seen from the front--consider paying a visit here during a Chicago weekend getaway!

Finish your long weekend in Chicago at River North.

River North is the area just north of the Chicago River. Whoever named it wasn’t very creative, but they were very accurate.

River North is absolutely FULL of awesome bar and restaurant destinations. As with many neighborhoods in Chicago, the best way to experience it is by hopping from place to place. When you find a place you love, stay as long as you’d like, then move along to the next place! That is the Chicago way of experiencing the nightlife.

Chicago is an enormous place, sprawling for miles and miles. The downtown area has many neighborhoods, each of which has pros and cons for visitors to the Windy City.

The best places to stay for 3 days in Chicago are near the Chicago River, specifically River North, Gold Coast, Streeterville, and The Loop.

In addition to those, a few more great neighborhoods are Lakeview, Lincoln Park, West Loop (which is home to great Chicago street art ), Near North, and Old Town.

Here are a few great hotel recommendations for budget, mid-range, and luxury travelers.

Classic Chicago Ilinois Theater sign

Godfrey Hotel — The Godfrey Hotel is in the River North neighborhood, and is right in the middle of many of the best activities on your 3 day Chicago itinerary. On top of the great location, the hotel is beautiful on the inside and gets excellent reviews. The Godfrey Hotel is a wonderful place to hang your hat while exploring Chicago.

Check rates & book your stay at The Godfrey Hotel today!

Hyatt Regency Chicago — The Hyatt Regency Chicago is located in The Loop neighborhood, right on the Chicago River.

Many of the rooms in the Hyatt Regency have beautiful views of the Chicago River, the skyline, and the city streets.

The rooms are wonderful, the price is good, and the location is excellent. Additionally, the fitness center, meeting rooms, an on-site bar and restaurant, and access to Chicago activities make the Hyatt Regency one of the best places to stay in Chicago.

Check rates & book your stay at the Hyatt Regency Chicago today!

The Langham — Now, to the creme de la creme. If you’re a luxury traveler looking for the best hotel in Chicago, look no further than The Langham.

First off, the location could not be better. Located right on the Chicago River in River North, you’ll be within walking distance of nearly everything on your itinerary.

Additionally, The Langham pulls out all the stops when it comes to amenities. The on-site spa, fitness center, pool, and deluxe bar and restaurant are all five stars. Of course, the rooms are wonderful as well, and nearly all have stunning views of the cityscape.

Check rates & book your stay at The Langham today!

Chicago Skyline with river filled with sailboats in the center, an excellent view to seek out during 3 days in Chicago

Chicago and food go hand in hand. You could explore a new food destination in Chicago every night for the rest of your life, and not eat at the same place twice. Not going to fact check that, but it is probably true. There are awesome restaurants on every corner, all across the city!

Here are four must-visit restaurants in Chicago that we love. 

Chicago-Style Pizza – Giordano’s

You can’t come to Chicago and not try some Chicago-style pizza. You literally can’t, it is impossible. The best Chicago-style pizza is at Giordano’s. The pizza here is absolutely LOADED with cheese and toppings, more than you have ever had, guaranteed. One slice and you’ll be satisfied, two slices and you’ll be stuffed. Be prepared to have leftovers!

Portillo’s is a Chicago institution. This started as The Dog House, a hot dog stand, and grew into Portillo’s, a delicious restaurant serving beef, burgers, and Chicago-style hot dogs all across the city. Portillo’s is yummy, quick, and is a Chicago must. Try the chocolate cake shake, you’ll be glad you did.

Chicago-style hot dog displayed on a red checkered napkin

Happy Camper

Happy Camper is an excellent classic pizza place located in the Near North neighborhood, which offers an excellent atmosphere. This is a great place to watch sports, meet friends, enjoy a happy hour, and of course, try some pizza!

The toppings are creative at Happy Camper, and the pizza is DELICIOUS. There is also a huge selection of local and imported beers to try.

Girl and the Goat

Girl and the Goat is an absolutely EXCELLENT restaurant located in the West Loop neighborhood on Randolph Street. T he food here is delicious and is very creatively and expertly prepared.

Call ahead for a reservation at Girl and the Goat, as there may be a long wait if you just show up asking for a table. If you do just show up, however, this is worth the wait.

And you can walk across the street to one of the many bars on Randolph while you wait for a table at Girl and the Goat!

Zach and Julie Ruhl at The Bean in Chicago

Bonus: take a Chicago food tour!

In a city as centered around food as Chicago, taking a food tour is one of the best ways to explore the city’s cuisine. 

Not only will you be able to sample a wide variety of classic dishes without committing to a whole portion, you’ll also learn plenty about Chicago’s history and culture along the way!

This popular food tour gets rave reviews and is an excellent addition to your long weekend in Chicago.

Book your food tour in Chicago today!

Deep Dish Pizza in Chicago being sliced and served, one of the most important foods to eat during your 3 day Chicago itinerary!

Getting around for 3 days in Chicago is in most ways easy, but can sometimes be challenging.

The public transport system is the easiest and most inexpensive way to get around, followed by cabs/Uber/Lyft, and finally driving yourself.

Much of the 3 days in Chicago itinerary laid out above, however, can all be completed by exploring on foot, especially from the recommended hotels. The awesome destinations and great parks are relatively close together and can be reached with a nice walk in the Chicago air.

Chicago has one of the best public transport systems in the US. The elevated train, AKA the ‘L’, brings people across Chicago east, west, north, and south. The ‘L’ stops at all of the amazing sites in the city, as well as O’Hare Airport, Midway Airport, and all the major thoroughfares.

If you would rather avoid public transportation, then the best way to travel around during this 3 day Chicago itinerary is with a cab/Uber/Lyft. Traveling this way is likely the fastest if you can avoid rush hour, and the most convenient. However, it will be more expensive than using the ‘L’ trains.

Finally, you, of course, have the option of driving yourself around town. In our opinion, this is the most stressful way to get around, as you’ll have to worry about parking in the busy downtown streets. This is a challenge and is made worse considering that many hotels offer parking fees.

Photo of Chicago train traveling on a bridge over car traffic--using Chicago's public transportation is the best way to get around on a Chicago weekend getaway!

The best time to plan a long weekend in Chicago is during the summer. The weather during the summer is absolutely perfect, and it’s definitely the easiest time to pack light for a Chicago vacation (if you visit during the blustery winter, be sure to carefully consider what to wear in Chicago !). This is also the best time to explore the awesome parks, beaches, and outdoor destinations in the Windy City.

Each year in the summer, Lollapalooza brings huge crowds looking for an awesome time and great music. Lollapalooza draws many of the best music acts in the world, so traveling to Chicago during the music festival is a great opportunity. On top of this festival, many great music artists perform regularly at Wrigley Field, Soldier Field, the United Center, and the other great venues across Chicago.

Coming in a close second to the Chicago summer is the spring when the city defrosts after its long Chicago winter and comes alive. There is nothing quite like spending 3 days in Chicago when the atmosphere is on the rise, as it is in spring.

Also during this time is St. Patrick’s Day, one of the largest holidays in Chicago. On St. Patrick’s Day the river is dyed bright green, and the partygoers are out in force.

4 photos of Chicago Illinois: skyline, beach, theater sign, deep dish. Black and red text on a white background reads "How to spend 3 days in Chicago"

4 thoughts on “3 Days in Chicago: The Ultimate Weekend in Chicago Itinerary”

I’d like to follow for future information

Thanks for this comprehensive guide! It made planning a trip to Chicago so much easier!

As a frequent traveler to Chicago, who lives just a few hours away, I want to mention a few places that truly make Chicago iconic. The Palmer House Hotel is the best in the City. Right outside the doors of the Palmer House is a Chicago favorite, with a long history, called Miller’s Pub. Grab an Allagash White beer on tap – a local favorite. Don’t miss a food tour of Chinatown. There is so much history there, and the food is really amazing! Other amazing foodie spots in Chicago are Bongo Room for brunch and Cafe Babareba for Spanish style tapas (do not miss the baked goat cheese in tomato sauce). An architectural tour on the Chicago River is a lovely way to spend the day and if that isn’t your thing, the water taxis are a fun way to get around.

Agrred with the other poster–This itinerary is hugely missing the architecture tours! Best thing to do in the city. River north is fine, but kind bro-y for lack of a better descriptor. Bongo room is in Wicker Park which I describe as our Williamsburg. Not quite as artsy and cool as it was 5 years ago but still very fun!

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Chicago in a Day: Iconic Parks, Art, and Skyline Views

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February 7, 2024 · 1 min read

Chicago 1 Day Itinerary

Embark on a whirlwind tour of Chicago's most celebrated landmarks with our one-day itinerary. Start your journey at Millennium Park, a vibrant green space in the heart of the city, where you can admire the famous Cloud Gate sculpture and enjoy the lush surroundings for about 2 hours. Next, immerse yourself in the world of fine arts at The Art Institute of Chicago, one of the leading art museums globally. Allocate the bulk of your day here to explore its extensive collections. Conclude your day with breathtaking views from the Willis Tower's observation deck, where the city's skyline unfolds before you. This 2-hour visit to one of the tallest buildings in the world will leave you with lasting memories of Chicago's architectural grandeur.

hotelStar

  • Day 1: Exploring the Heart of Chicago's Splendor

Millennium Park

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Begin your Chicago adventure at the iconic Millennium Park, a verdant oasis nestled amidst the city's bustling streets. As the first stop in your itinerary, allot roughly two hours to meander through this urban sanctuary. The park is renowned for its cutting-edge art installations, lush landscapes, and the famous Cloud Gate sculpture, affectionately known as 'The Bean.' Engage with the vibrant cultural scene and perhaps catch a glimpse of a live performance at the Jay Pritzker Pavilion.

Attraction Info

  • 201 E Randolph St, Chicago, IL 60602, United States
  • Suggested tour duration: 2-3 hour
  • Open from 6:00am-11:00pm

Recommended Nearby Restaurants

The Signature Room at the 95th

The Art Institute of Chicago

Next, immerse yourself in the world of fine arts at The Art Institute of Chicago, a premier art gallery that demands the better part of your day. Housing an impressive collection that spans thousands of years, the institute offers a journey through a multitude of art forms, from ancient artifacts to contemporary masterpieces. Stand before the works of Monet, Van Gogh, and many other greats, and let the beauty of human creativity wash over you in this temple of art.

  • 111 S Michigan Ave, Chicago, IL 60603, USA
  • Suggested tour duration: 0.5-1 day
  • Closed on Tue-Wed;Open on Thu,11:00am-8:00pm;Open on Mon, Fri-Sun,11:00am-5:00pm

Willis Tower

Conclude your day on a high note at Willis Tower and its sky-high observation deck. As the sun begins to set, ascend to the Skydeck and witness the sprawling cityscape transform with the golden hues of dusk. The panoramic views from one of the tallest buildings in the Western Hemisphere are nothing short of breathtaking. Spend a couple of hours here, capturing the memories and the skyline, as you reflect on a day well spent in the Windy City.

  • 233 S Wacker Dr, Chicago, IL 60606, United States
  • Open from 3/1-9/30,Mon-Fri,9:00am-10:00pm;Open from 10/1-2/28,Mon-Fri,9:00am-8:00pm;Open from 10/1-2/28,Sat-Sun,9:00am-10:00pm;Open from 3/1-9/30,Sat-Sun,8:30am-10:00pm,Please refer to the official website for details of holiday opening hours; the specific business status is subject to the opening conditions on that day.

Where to Stay Tonight

Hilton garden inn chicago central loop, canopy by hilton chicago central loop, w chicago - city center, jw marriott chicago, top things to do in chicago-2024.

The Art Institute of Chicago

* All user reviews in this article have been translated by machine.

* The information above is subject to change at any time. For the latest information, please check the websites of hotels and attractions.

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3 Days in Chicago: The BEST Weekend Itinerary (By a Local!)

Planning 3 days in Chicago and seeking the perfect itinerary? I have lived in Chicago almost my entire life so I have created the perfect detailed Chicago 3 day itinerary with the best things to do, best places to eat, where you should stay, and all of my top tips, so that you can spend less time planning and more time enjoying the Windy City.

There is so much to do in Chicago but three days is enough to see most of Chicago’s top attractions . I have grouped each day by neighborhood so you don’t have to waste time getting around.

3 Days in Chicago Itinerary

3 Days in Chicago Itinerary Travel Blog

3 Days in Chicago – Day 1

Lets start Day 1 in Chicago by enjoying some of the best views Chicago has to offer.

360 CHICAGO

For panoramic views of Chicago, head to 360 CHICAGO (formerly John Hancock Observatory), a public observatory on the 94th Floor of 875 N Michigan that offers breathtaking 360 degrees views of the city skyline and Lake Michigan.

The 360 Chicago observation deck is also home of TILT – Chicago’s highest thrill ride – an enclosed moving platform that literally tilts you out over Michigan Avenue from the 94th Floor.

Tip: 360 Chicago tends to be less busy and has shorter lines that the taller Willis Tower (on Day 2) but it is still best to visit in the morning to avoid crowds. (Click here to buy a skip the line ticket ).

Shop (or Window Shop) on the Magnificent Mile

After visiting 360 Chicago, walk south on Michigan Avenue and join the throngs of visitors and locals shopping (or window shopping) on The Magnificent Mile. The Magnificent Mile (or The Mag Mile), is an upscale section of Michigan Avenue, running from Oak Street to the Chicago River. Although some of the stores on Michigan Avenue are pricey, it is totally free to window shop. Landmarks on the Mag Mile include the historic Chicago Water Tower, the Tribune Tower and the Wrigley Building skyscraper.

Take an Architecture River Cruise

3 day weekend in chicago

Chicago has amazing architecture and the best way enjoy it is by taking an architecture river cruise . Because the water sometimes freezes, river cruises don’t usually run in the winter.

If you are visiting Chicago in the summer, you can do a longer combined architecture river and lake cruise to see the skyline from the lake as well.

best things to do chicago travel blog

An alternative to a river cruise is to take a walk along the Chicago Riverwalk . The Riverwalk is one of the best spots in Chicago for people watching and there are also restaurants , shops and places to sit along the way. You can see a map of attractions on the Riverwalk here .

Go on a Gangsters Tour

Chicago has a long  history of organized crime and is famous for being the home of mafia figure Al Capone. There are many mob tours for those that want to learn more about the history of organized crime.

Food or Drinks with a View

Chicago has several rooftop bars and restaurants with amazing views of Chicago.

Cindy’s (12 S Michigan Ave) is a restaurant and bar on the rooftop of the Chicago Athletic Association Hotel located across Millennium Park which offers panoramic instagram worthy views of Millennium Park and Lake Michigan. This is a popular spot and the wait for the elevator can be long but if you visit around the time it opens (10 am on the weekends and 11 am on some weekdays) you can enjoy the great views without the crowds.

LH ON 22 (85 East Wacker Drive) -Enjoy classic cocktails and small bites from the outdoor LH terrace of LondonHouse Chicago which offers great views of the Chicago River, Lake Michigan and the Magnificent Mile.

The J. Parker (1816 N Clark St) is a stylish bar and restaurant on the rooftop of the Hotel Lincoln with great views of Lincoln Park.

3 Days in Chicago – Day 2

From the highest vantage point of the city to the famous Bean, Day 2 in Chicago will take you to Chicago’s best and most famous attractions.

Skydeck at Willis Tower

The Skydeck at Willis Tower (formerly known as the Sears Tower and what locals still call it) is the most well known of Chicago’s two tall skyscrapers with public observatories. The Willis Tower is the tallest building in the Western Hemisphere and was the tallest building in the world from 1974 until 1998.

If you are not scared of heights, you can stand on the Ledge’s glass boxes that extend out over 4 feet from the Skydeck.

Tip:   Lines for the Skydeck can get very long (especially on weekends) so avoid the crowds it is best to visit first thing in the morning as soon as it opens or in the evening. (Click here to buy a skip the line ticket ).

See The Bean at Millennium Park

The Bean at Millenium Park is a must on any three day in Chicago itinerary

If you have seen photos of Chicago on social media, chances are you have seen photos of Cloud Gate (also called The Bean), the famous mirrored sculpture in Millennium Park.

Please note that due to construction, public access and views of Cloud Gate are limited through spring of 2024.

Although The Bean is very touristy, don’t skip it. It is one of the most instagrammable places in Chicago and it is a great spot to take photos to remember your trip to Chicago.  The Bean is usually crowded especially in the summer and on weekends so if you don’t want other people in your photos visit early in the morning.

The free Millennium Park is part of Grant Park and also includes the Jay Pritzker Pavilion, the Crown Fountain sculpture and Lurie Garden. In the winter, there is a free ice skating rink right in front of the park. On hot summer days, kids (and some adults) love to splash in the water from the Crown Fountain .

millenium park which includes crown fountain is a Chicago must do

If you are visiting Chicago with toddlers and young kids, you might want to also visit Maggie Daley Park , a large public park connected to Millennium Park that has play areas for kids of various ages, a fieldhouse, climbing wall and another ice-skating ribbon in the winter.

Art Institute of Chicago

Chicago has many great museums which are worth visiting but my top pick is the  Art Institute of Chicago conveniently located next to Millennium Park. It is one of the oldest and largest art museums in the United States and is frequently found on lists of the top museums in the world. (Click here to buy a skip the line ticket if you want to avoid long lines).

a perfect three day in Chicago itinerary includes Navy Pier

Some locals consider Navy Pier a bit of a tourist trap, but it is a not to missed attraction especially for those visiting Chicago with kids. Navy Pier is full of fun things to do including a large Ferris wheel, rides and games, the Chicago Children’s Museum and several shops, restaurants (including Giordano’s and Garrett Popcorn Shops) and bars. Navy Pier is also the starting point for various sightseeing cruises and boat rides.

Tip: If you are visiting Chicago in the summer, stay or come back for the free fireworks at Navy Pier every Wednesday at 9 pm and Saturday night at 10 pm. You can even watch the show from the water on a sightseeing cruise .

3 Days in Chicago – Day 3

Here are my suggestions for your third and final day sightseeing in Chicago. If you are visiting Chicago on a Sunday morning, head to Maxwell Street Market , one of the best places for Mexican food.

chicago day trip itinerary

Visit One or More Museums

Chicago has many great museums which are worth visiting. The Field Museum , the  Shedd Aquarium and Adler Planetarium are all located close to each other on The Museum Campus. The Adler Planetarium Skyline Walk has one of the best skyline views of Chicago .

cherry blossoms in front of Museum of Science and Industry in Chicago

The Museum of Science and Industry is located in Hyde Park and is a bit out of the way from downtown Chicago but it is a really fun museum with hands-on activities and interactive exhibits. If the weather allows and you have extra time in Hyde Park, you might want to check neighboring Jackson Park . This park has cherry blossom trees in the spring and it also has a free Japanese garden.  Promontory Point is about a half mile away and has great skyline views of Chicago.

Tip:   If you are visiting a few museums and indoor attractions, consider purchasing a Chicago CityPASS or Go Chicago Card to save money on entrance fees.

Explore the Lakefront Trail and Beaches

people walking and relaxing on the Lakefront Trail in Chicago

Chicago’s Lakefront Trail is a paved path on a 18-mile-long stretch along Lake Michigan and it is a great spot to people watch and get some exercise.  In the summer and weekends, the lakefront is packed with locals and visitors walking, running and riding bikes.  You can find a map with the access points here .

Most people don’t think of Chicago as a beach destination but Chicago has many beaches on Lake Michigan.   Oak Street Beach and Ohio Street Beach are conveniently located close to the major tourist attractions. North Avenue Beach is more of a party beach and is located close to Lincoln Park.

More Things to Do in Chicago

If you have more time or not a fan of museums or tall buildings, here are some more fun things to do in Chicago:

Find Street Art

Moose Bubblegum Bubble by Jacob Watts one of the most famous street art murals in Chicago

Chicago is full of street art and there are always new murals popping up.  One of the most famous Chicago murals is “Moose Bubblegum Bubble” (pictured above) by Jacob Watts which located at 33 E. Ida B. Wells Drive (formerly 33 E. Congress Parkway). It is part of the Wabash Arts Corridor which is walking distance to Millennium Park, The Art Institute of Chicago and other well known tourist attractions. You can find more detailed mural walks in the Loop here .

Another famous mural is The Greetings From Chicago Mural at 2226 N Milwaukee Ave, in Chicago’s Logan Square neighborhood. You can see this mural and other street art on this street art tour .

Another neighborhood that has a high concentration of street art (as well as great Mexican food) is Pilsen.

Watch a Cubs Game at Wrigley Field (or attend another sporting event)

what to see in Chicago

Chicago is known for their love of their sports teams, so if you are visiting during the season you might want to attend a sporting event. To those unfamiliar, historic Wrigley Field is home to one of the city’s baseball teams – the Cubs.  Whether a fan of the Cubs, baseball in general or just a fun atmosphere, a day at the 100 year old ballpark is a must for locals and tourists alike.  You don’t need to enjoy baseball to enjoy a Cubs game – it is fun to just soak in the atmosphere while drinking and eating. (There are also tours of the stadium offered during the off season).

Enjoy One of Chicago’s Many Festivals

Chicago always has at least one or more festivals or events happening every weekend especially in the summer .  Some Chicago festivals are very well known and attract thousands of tourists, but there are many festivals and events in Chicago where you will mostly find locals. For great food, music and people watching, check to see if there are any festivals or events  going on while you are in town.

Walk The 606

The 606 is Chicago’s version of The Highline in NYC , an elevated trail goes through 2.7 miles of the city’s northwest side neighborhoods: Wicker Park, Bucktown, Humboldt Park, and Logan Square.  It is a bit off the beaten tourist path but it great place to walk, run or bike.  There are several access points so you can get off the trail to explore the various neighborhoods.

Where to Eat in Chicago

Chicago is known for its food so get ready to eat! Chicago is one of the best cities in the world for food and I could easily write a whole post just about the food! Although Chicago is famous for food like deep dish pizza and Chicago-style hot dogs – there is so much more great food in Chicago.  Don’t limit yourself to just deep dish pizza and hot dogs, but you should try those if you are visiting Chicago for the first time.

Lou Malnati’s and Giordano’s  are two of the best restaurants for deep dish pizza. Giordano’s can be found in several spots throughout the city including Navy Pier, near Michigan Avenue and near Millennium Park.

Many locals consider Pequods in Lincoln Park to have the best deep dish pizza in Chicago. Their version has a caramelized crust.

For Chicago style hot dogs (remember, no ketchup allowed) try Portillos , a popular chain.

Al’s Italian Beef (169 W Ontario St.) is famous for its Italian beef sandwiches.

For original Chicago-style popcorn head to Garrett Popcorn Shops, with a location near Millennium Park and Navy Pier.

To get an overview of the food scene consider a food tour:

Where to Stay in Chicago

Most people visiting Chicago stay in the downtown area including the Loop, River North, Gold Coast, Streeterville and Michigan Avenue since they are close to most of the major tourist attractions. If you are visiting during the weekend, the Loop is a great option as it is more quiet at night. River North (where I live) is close to nightlife and restaurants, but noise can be a problem especially during the weekends. Here are some of my top picks for the best hotels in Chicago :

The Peninsula Chicago.   If you are looking for a luxury hotel, The Peninsula Chicago is one of the best hotels in Chicago with a world renown spa and a half-Olympic length swimming pool overlooking the Chicago skyline. It has a central and convenient location right off the Magnificent Mile, close to shopping and less than a block from the Water Tower and 360 Chicago. Click here to see the latest prices and click here to read reviews .

Hilton Chicago/Magnificent Mile Suites.  Recently renovated all-suite hotel with fridge and microwave in room. Great location just steps from Michigan Avenue and one block from Lake Michigan.   Click here to see the latest prices and click here to read reviews .

ACME Hotel Company. This modern, stylish and unique hotel is located in downtown Chicago 2 ½ blocks from the Magnificent Mile in River North. Offers great value and great service. Click here to see the latest prices and click here to read reviews .

Best Western River North Hotel. Convenient located in the heart of River North close to the Chicago River as well as many restaurants and bars. Amenities include free high-speed Wi-Fi, deeply discounted parking, room service, fitness center, indoor pool and sun deck.  Click here to see the latest prices and click here to read reviews .

The Best Time to Visit Chicago

Chicago has plenty of things to do year round whatever the season. Summer is one of the best (and busiest) times to visit Chicago as the city comes alive and there are always outdoor festivals, concerts and events going on where you can take advantage of the warm weather. Restaurants and bars open their rooftops and sidewalk patios so you can dine outside. The temperature in the summer is usually hot but not unbearable (but some days can be very hot and muggy).

Winter can be very cold and snowy but some years can have mild winters with hardly any snow. Late November and December are busy with holiday events and festivities and the temperatures are usually still not that cold.  January and February tend to be the coldest months but attractions are less crowded. Even if you hate cold weather, there are enough indoor attractions to keep you entertained in Chicago during the winter .

Fall and spring are generally great times to visit Chicago – the popular attractions are not as busy as summer and the weather is usually more pleasant (but temperatures can be very unpredicable). The weekend before St. Patrick’s Day and the weeks during spring break can get very busy but the rest of spring is considered shoulder season.

Personally, I think the best time to visit Chicago is September and early October because students are back in school but temperatures are still warm but not as hot and humid as summer.

If you still need help deciding when to visit Chicago, check out The Best Time to Visit Chicago – A Month By Month Guide  for more details regarding weather and events by month.

Getting Around in Chicago

Chicago is an easy city to get around in with many public transportation options. Both Chicago airports – Chicago O’Hare (ORD) and Chicago Midway (MDW) – are connected to downtown Chicago by train.

For longer distances you can use public transportation , taxi, rideshare or rent bikes through Divvy (Chicago’s bike share program).

Taxis are plentiful and very easy to find downtown and at popular tourist attractions. You can also use the Curb app (for taxis) or ridesharing apps ( Lyft and Uber) to get around Chicago .

A hop on hop off bus is a great way to see all the attractions without having to figure out how to get around.

These are my top choices for the best things to do if you have 3 days in Chicago .

Planning a trip to Chicago? Check out more of my Chicago guides and itineraries:

  • Best Things to Do in Chicago in the Summer
  • 24 Hours in Chicago: A Perfect One Day Itinerary (From a Local)
  • Most Instagrammable Places in Chicago
  • Best Free Things to Do in Chicago
  • Best Day Trips From Chicago

3 Day Itinerary for Chicago From a Local

Related Posts

BEST Things to Do in Chicago This Weekend

savvyglobetrotter

One comment.

Hi, I have also lived in Chicago and yes, although Summer is great, the best time to visit I’d also say it’s Aug/Sept. This is one, if not THE one, of the best places on Earth. I’d even say, if you can stay longer than 3 days in Chicago, do so. You are not going to regret it, since the city offers so much to do year round. Lovely post!

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The Ultimate Chicago Family Vacation | 3 Days in Chicago With Kids

This post may contain affiliate links, view our disclosure policy .

Look no further for the ultimate Chicago family vacation itinerary perfect for spending 3 days in Chicago with kids!

The magnificent city of Chicago receives recognition as being the ‘Best Big City in the U.S.’, as well as being the ‘#1 World’s Best City for Having it All’ .

In this post, you’ll learn about what to see and do, how to get around, and how to plan a 3 day Chicago itinerary when visiting Chicago with kids.

In addition, our Chicago family vacation itinerary will guide you to the most popular things to do in Chicago while helping you plan the best visit ever!

The links on this page are Amazon affiliate links. If you click on the links and make a purchase, I receive a small commission at no extra cost to you.

Chicago 3 day itinerary featured by top US family travel blog, Travel with a Plan.  Start planning your Chicago family trip now!

Table of Contents

Chicago Family Vacation

If you’re wondering, “Is Chicago a good family vacation spot?”, I would overwhelmingly say, “Yes!”.

In fact, if you’re familiar with popular urban vacation destinations, it’s more than likely that Chicago is on your  US bucket list !

Located on the shore of Lake Michigan in Midwest USA, Chicago, Illinois is a glorious city with a population of 3 million people.

Chicago is a tourist’s dream as it has a magnificent, walkable downtown area filled with gorgeous parks and sculptures, impressive museums, several  famous Chicago foods , and beautiful lakeside views.

Perfectly blending the hustle and bustle of city life with a degree of friendliness that you’d expect from a small town, this diverse area is a must-visit metropolitan wonder.

Whether you’ve dreamed of walking through Millennium Park and photographing “The Bean” or you want to enlighten your kids by checking out the ever-popular Adler Planetarium, there are so many family-friendly Chicago attractions!

Oh, and psst…we LOVE Chicago so much, that we’ve written several other guides to help you plan your trip!

  • What to Wear in Chicago: A Visitor’s Guide for Every Season!
  • What to do in Chicago in Winter (+ 3-Day Itinerary)
  • Top 5 Kid-Friendly Restaurants in Downtown Chicago
  • 25 Things to do in Chicago at Night
  • A Complete List of Things to do at Navy Pier Chicago
  • Famous Chicago Food: 5 Iconic Chicago Foods to Try!

Best Time to Plan A Chicago Vacation

The best time for a Chicago family vacation is during the months of May, June, September, and October.

In other words, plan a family trip to Chicago when the weather is mild during the late spring, early summer, and early fall.

In addition, be sure to consider what to wear in Chicago depending on when you visit, as the weather varies drastically.

Though Chicago in summer can be hot and humid, many are drawn to the area during this time in order to take advantage of its lake activities and outdoor events.

Keep in mind, however, that Chicago gets very busy with tourists over the weekends and holidays.

We just so happened to visit Chicago in September over Labor Day weekend.

Though the sidewalks throughout the city were very crowded, the holiday weekend special events still made this a great time to visit.

Additional planning tip: If you’re not afraid to get bundled up and brave the cold, we’ve found that visiting Chicago in winter can be just as fun!

Read here to learn about our winter getaway in Chicago which includes the best things to do in Chicago in winter .

Chicago Family Vacation Itinerary: Day 1

The following breakdown of several family activities in Chicago can be applied to a two-day itinerary for Chicago, or extended to a 4-day Chicago itinerary.

Either way, here are our favorite Chicago vacation ideas that we’ve done time and time again.

  • Arrive in Chicago and admire the beautiful Chicago skyline
  • Check-in to your hotel
  • Have dinner at the iconic Portillo’s Hot Dogs

Arrive In Chicago

Day 1 of our 3-day Chicago family itinerary involved a 6-hour drive from our hometown (We love road trips!)

We found travel down Interstate 90 and into the heart of downtown Chicago to be an absolute breeze, with the exception of heavy traffic at times.

Considering driving to the Windy City too?

We have compiled essential tips on how to master a family road trip , and how to create “Are We There Yet” goodie bags to help make it the best road trip ever!

Chicago 3 day itinerary featured by top US family travel blog, Travel with a Plan: image of Chicago Best Western rooftop deck

Check-In To Your Hotel

For this Chicago family vacation, we stayed at the Best Western River North .

Best Western River North is centrally located to several downtown Chicago points of interest.

It is also really close to some great places to eat with kids, such as the SafeHouse, Portillo’s, McDonald’s, and Hard Rock Cafe.

Also adjacent to Best Western River North is a BP gas station and Walgreen’s pharmacy and convenience store.

Check-in was quick and efficient and the front desk staff was very friendly.

They even offer free ice cream sandwiches and sherbet push-ups around the clock!

Like most hotels downtown, there is a daily fee to park on-site. The lot is staffed by a parking attendant and is safe and secure.

Our room was comfortable and stylish; just large enough for 2 double beds and an additional cot. The hotel itself has a heated indoor swimming pool on the top floor.

Next to the pool is an outdoor rooftop deck with comfortable lounging chairs and amazing views of the city.

We loved taking a glass of wine up to the deck each night to relax while the kids swam. The presence of the rooftop deck was definitely the best selling point for us.

Breakfast is not included at Best Western River North, but for a small cost, you can visit the onsite restaurant for made-to-order breakfast items.

Portillo’s

No family trip to Chicago is complete without experiencing the 5 famous Chicago foods that are the cornerstone to every visit.

Being right across the street from our hotel, Portillo’s was an easy choice to start off our epic Chicago food experience.

What started as a hot dog cart, Portillo’s restaurant serves up Chicago-style hot dogs, Italian beef sandwiches, burgers, salads, and other sides.

Their casual atmosphere, amazing food, and welcoming ambiance make this one of our most recommended kid-friendly restaurants in downtown Chicago .

Additional planning tip: If you’re looking for a complete foodie experience, schedule a Chicago Food Planet walking food tour that covers the Chicago hot spots.

Chicago 3 day itinerary featured by top US family travel blog, Travel with a Plan: image of Portillo's restaurant

Chicago Family Vacation Itinerary: Day 2

  • Walk and shop on Magnificent Mile
  • Take an Architectural River Cruise
  • Have lunch at Wildberry Pancakes and Cafe
  • Tour and take photos in Millennium Park
  • Spend time enjoying Navy Pier

Magnificent Mile

Start off your Chicago family trip by grabbing a cup of coffee and taking a leisurely walk along Chicago’s Magnificent Mile .

Magnificent Mile is the nickname of the long stretch of upscale shops and restaurants located along Michigan Avenue.

It is also home to the world-famous John Hancock building (home to 360 Chicago and TILT) and the historic water tower and pumping station that were two of the only structures to survive the Chicago Fire of 1871.

Walking along the bustling sidewalks of the Magnificent Mile is not to be missed in your Chicago 3 day itinerary.

Kid-friendly stops include the Disney Store, American Girl Place, Chicago-famous Garrett P opcorn , and Dylan’s Candy Bar.

Chicago 3 day itinerary planning tips: Depart your hotel at 9:30 AM on foot.

Plan to spend 20 minutes walking the entire Magnificent Mile from north to south, with additional time allotted for your choice of shopping and stops.

View this post on Instagram Our experience on Chicago Architecture Center’s River Cruise aboard Chicago’s First Lady was nostalgic, informative, relaxing, and overall AMAZING! So thankful for this opportunity! #choosechicago #cruisechi2019 #cruisechicago #cafcrivercruise #travelwithaplan #TWAP #familytravel #chicagowithkids A post shared by Jennifer Brommer (@travelwithaplan.jen) on Aug 31, 2019 at 5:50pm PDT

Architectural River Cruise

If you’re looking to plan a family vacation in Chicago, IL, our top recommendation is to get tickets to go on a Chicago architecture river cruise (if the weather and season permit).

After walking down Magnificent Mile to the south, you will come across the Michigan Avenue Bridge and Chicago’s Riverwalk.

Here is where you access the Chicago Architecture Foundation Center River Cruise aboard Chicago’s First Lady .

For GPS directions, use 112 E. Wacker Drive and look for their blue awning marking the stairway down the river walk dock.

Though there are a few other river cruise options, we absolutely loved our experience on the CAFC River Cruise and highly recommend it.

The boat was family-friendly, fun, and nostalgic, and the commentating was highly informative.

There is a full bar aboard that includes snacks, drinks, and cocktails.

Imagine a glorious float down the Chicago River learning about the towering skyscrapers – while sipping a Mimosa with Tony Bennett music playing in the background.

Chicago family vacation planning tips: Secure 10:30 AM CAFC River Cruise reservations .

Pick up your tickets at 10:00 AM and get in line no later than 10:15 AM to be the first to board the First Lady.

Seats are not pre-assigned and are first-come-first-serve.

Choose seats on the upper deck along the sides for the best-unobstructed photo ops.

The entire river cruise lasts 90 minutes.

chicago day trip itinerary

Millennium Park

No vacation in Chicago would be complete without visiting Millennium Park! In addition, if you’re planning a family trip to Chicago on a budget, it’s nice to know that all of the attractions in Millennium Park are free!

After stopping for lunch at Wildberry Pancakes and Cafe , spend plenty of time visiting Chicago’s iconic Millennium Park .

Here is where you will find the most talked-about (free) attractions that people typically refer to when visiting Chicago.

Each of these attractions should be part of any Chicago trip with the family!

Chicago 3 day itinerary featured by top US family travel blog, Travel with a Plan: image of The Bean

The most popular attraction in Millennium Park is the Cloud Gate sculpture.

Commonly referred to as ‘The Bean’, Cloud Gate is an art piece that is a great place to take Instagram photos and selfies, especially off of its reflective surface.

You can see the reflection of the Chicago skyline, walk under The Bean, and take photos from all sides.

Despite the crowds, the space is large enough to accommodate large amounts of visitors.

(It is highly unlikely to get a photo without other tourists in it, however.)

Chicago 3 day itinerary featured by top US family travel blog, Travel with a Plan: image of Crown Fountain

Crown Fountain

Another highlight of Millennium Park is Crown Fountain .

Here, two huge 50ft LED screens light up while displaying the faces of average Chicago residents.

Every 5 minutes, the mouths of the faces spill water onto the ground creating a shallow reflective pool.

The fountains make a great place for kids to cool off in the hot summer months.

BP Pedestrian Bridge

The gigantic stainless steel BP Bridge connects Millennium Park to Maggie Daley Park.

Though there are other outlying sidewalks to get to Maggie Daley Park, make it a point to walk across this unique pedestrian bridge.

Its shiny silver surface, snake-like curvature, and prize-winning architecture make it an experience to remember.

Chicago 3 day itinerary featured by top US family travel blog, Travel with a Plan: image of Maggie Daley Park

Maggie Daley Park

As one of the most kid-friendly Chicago activities, be sure to visit Maggie Daley Park!

After crossing BP Pedestrian Bridge you will enter Maggie Daley Park .

Here you will find mini-golf, a climbing wall, and 5 playgrounds themed for different ages and abilities.

Large tube slides for older kids, innovative swings, and a splash fountain for younger ones are a few other highlights.

The rolling hills and valleys of rubber turf, as well as perfectly incorporated green space, make this a dynamic area that will keep kids entertained for hours.

For those families with small children or kids of all ages for that matter, Maggie Daley Park is a must-do during your Chicago itinerary.

Chicago 3 day itinerary featured by top US family travel blog, Travel with a Plan: image of Chicago lakewalk

Lakefront Trail

Upon exiting Maggie Daley Park and heading towards the water you will come across an entrance onto Chicago’s Lakefront Trail .

Chicago’s scenic Lakefront Trail is an 18-mile paved trail that follows along the shoreline of Lake Michigan.

With separate lanes for walking, running, and biking, head north on this trail from the Millennium Park area to get to Chicago’s Navy Pier.

The 15-minute walk along Lakefront Trail will allow you to admire Lake Michigan and watch the on-water boats, kayaks, and wildlife.

Chicago family vacation planning tip: Plan to spend 1-2 hours visiting Millennium and Maggie Daley Park.

You may need more time if you have smaller children who want to spend more time at the park.

Chicago 3 day itinerary featured by top US family travel blog, Travel with a Plan: image of Chicago Navy Pier

When considering what to do in Chicago in 3 days, no family itinerary is complete without a visit to the historic Navy Pier .

Over the past few years, Navy Pier has become one of the most popular things to do in Chicago as well as is one of the best Illinois attractions for families.

Likewise, there are literally so many things to do at Navy Pier Chicago with kids!

Ride the 200ft tall iconic Centennial ( Ferris ) Wheel and other outdoor amusement rides, or dine at one of its many restaurants.

Other activities at Navy Pier include the Amazing Chicago Funhouse Maze, Virtual Rush: Chicago virtual reality experience, and Lake Michigan sightseeing cruises.

Additional planning tip: If you’re looking for things to do in Chicago at night , save riding the Centennial Wheel for when the sun goes down!

Riding the Centennial Wheel at night is super fun and provides amazing views of Chicago’s lit-up skyscrapers!

View this post on Instagram One of the biggest highlights of our recent trip to Chicago was the #Chicagofoodplanet Signature Food Tour @ Navy Pier! Our amazing host Faith treated us to Navy Pier’s finest eats without having to wait in lines, and while humor and hospitality! A-MAZING! #chifoodplanet #chifoodplanettours #chicagofood #navypierfoodtour #navypier #chicagowithkids #foodplanet #travelwithaplan #TWAP #familytravel #bestplacestogo A post shared by Jennifer Brommer (@travelwithaplan.jen) on Sep 4, 2019 at 10:21am PDT

*Click here for our exclusive FREE Family Vacation Packing List that is both customizable and printable!

Family Packing Checklist

Chicago Family Vacation Itinerary: Day 3

  • Visit 360 Chicago and ride TILT
  • Take a Chicago Big Bus tour
  • Have lunch at Giordano’s Pizza
  • Tour the Art Institute of Chicago
  • Attend a Blue Man Group Chicago show
  • Have dinner at SafeHouse Chicago

Chicago 3 day itinerary featured by top US family travel blog, Travel with a Plan: image of 360 Chicago

360 Chicago Observation Deck + TILT

Start off this morning of your Chicago 3 day itinerary by walking through the north end of Magnificent Mile via Michigan Avenue (to Water Tower Place).

Here you find the (former) John Hancock building, which is home to the 360 Chicago Observation Deck and TILT.

Located on the 94th floor, the 360 Chicago Observation Deck provides unparalleled views of Lake Michigan and the Chicago skyline.

[Included in the Chicago CityPass ]

It also offers interactive learning opportunities, a gift shop, and a modern bar and cafe.

For an additional cost, visitors of the Observation Deck can ride TILT.

TILT involves stepping onto a moving platform that slowly tilts you – in a standing position – outside the side of the building.

As you hold onto metal bars, the platform moves outward in 3 increments until you are angled in suspension over Michigan Avenue and the buildings below.

Chicago 3 day itinerary featured by top US family travel blog, Travel with a Plan: image of TILT

Chicago itinerary planning tip: We had 9:00 AM reservations for 360 Chicago. This is a very popular Chicago attraction so I recommend visiting in the morning as such when crowds are fewer.

Plan to spend 45 minutes to 1 hour here.

Chicago Big Bus Tour

If you’re planning a trip to Chicago, we highly recommend doing a hop-on-hop-off Big Bus Chicago tour as a way to learn and see more of the city.

Tickets for Big Bus Chicago can be purchased online or at any of the advertised Big Bus stops .

There are 2 Big Bus Chicago stops on the same block as the John Hancock Building, so this is where we boarded and began our hop-on hop-off experience.

Chicago itinerary planning tip: It is important to refer to the Big Bus Chicago route map to plan the places and timing of your stops.

The lower half of the bus provides covered seating, while the top half of the bus is open air.

Rain ponchos are provided free of charge in the case of rain.

chicago day trip itinerary

Giordano’s Pizza

After boarding Big Bus Chicago at Stop #12, we rode continuously to Stop #4 at Millennium Park.

Here, we got off and headed for lunch at Giordano’s Pizza (130 E Randolph St, Chicago).

After having a slice of their famous deep-dish pizza while on the Navy Pier, we fell in love.

We couldn’t end our Chicago vacation without another round of this authentic Chicago-style pizza .

Additional planning tip: Plan to spend 1.5 hours at Giordano’s as the pizza alone take 45 minutes to bake.

Art Institute of Chicago

After lunch, we passed through Millennium Park to the adjacent Art Institute of Chicago .

One of the world’s greatest art museums, the Art Institute of Chicago goes out of its way to cater to families (+Kids under the age of 14 are free).

Our favorite family-friendly aspect was the Family Room.

Here, we got to create a customized family museum tour using the interactive Journey Maker.

Chicago itinerary planning tip: The Art Institute of Chicago is massive so plan to spend 60-90 minutes there, depending on the attention span of your kids.

Don’t forget to see Picasso’s, The Old Guitarist, and Grant Wood’s, American Gothic.

Chicago 3 day itinerary featured by top US family travel blog, Travel with a Plan: image of  Blue Man Group

Blue Man Group Chicago

After finishing our tour of the Art Institute, we grabbed an Uber and headed to the Briar Street Theater.

Briar Street Theater is home to Blue Man Group Chicago , and is stop #5 of our Chicago 3-day itinerary!

Having heard so much about Blue Man Group , we were so excited about this unique experience.

In fact, as soon as we stepped into the bustling dark theater adorned with blue spotlights, we knew we were in for a treat.

A performance filled with music, art, obscurities, and crowd interaction, the Blue Man characters wow the crowd without ever speaking a word.

Never knowing what is going to happen next, the performance is highly engaging and keeps you at the edge of your seat.

This unforgettable experience is a must-see upon your next family trip to Chicago!

Chicago itinerary planning tip: We had 2:00 PM reservations for Blue Man Group Chicago.

The performance lasts 90 minutes with no intermission.

Uber drivers were readily available to take us back to the downtown Chicago area once the show was over.

Additional planning tip: If you’re looking for another Chicago activity that teens will love, check out Escape Game Chicago! Though we have not personally done one, the downtown Chicago location offers 5 different 60-minute escape rooms!

Chicago 3 day itinerary featured by top US family travel blog, Travel with a Plan: image of  SafeHouse

SafeHouse Chicago

(This location is temporarily closed due to the effects of the pandemic; check their website before visiting.)

After heading to the hotel to rest and get changed for dinner, we walked 5 minutes to our much-anticipated dining experience at SafeHouse Chicago !

Once arriving at the secret entrance, couples, families, and groups are welcomed in one-by-one and must give a password in order to be granted access to the restaurant.

If you do not know the password, silly actions must be performed in order to be let in while the rest of the visitors in the restaurant watch on.

Once inside, the dark, spy-themed decor and lighting are uniquely inviting.

Upon being seated, you are immediately given a name tag to identify your ‘agent name’. This is the name that the servers will refer to you as during your dining experience.

After ordering off the menu, children may participate in an interactive scavenger hunt or visit the in-house magician while waiting for their food.

Chicago 3 day itinerary featured by top US family travel blog, Travel with a Plan: image of Safehouse bar lights

Chicago itinerary planning tip: Due to its popularity and that it is one of the best Chicago restaurants with kids, reservations are highly recommended at SafeHouse Chicago.

Also, you should know that t he fun doesn’t end once your meal is complete. (There is a mysterious twist in getting out of the actual restaurant.)

Chicago CityPASS

There are literally so many things to do in Chicago that many people wonder about Chicago family vacation packages.

One of our best travel tips is that if you’re trying to see the best of Chicago in 3 days, the most affordable way to see the city is with the  Chicago CityPASS .

In fact, you can save 50% on visiting Chicago’s top 5 attractions with this one purchase alone.

Grab your CityPASS here  – you will not regret bundling your activities into this Chicago family vacation package.

Additional planning tip: Most of the museums have a separate entry and line for CityPASS holders which will also save you a great deal of time.

chicago day trip itinerary

Chicago Family Vacation: Getting There

If you’re heading to Chicago with family, visitors typically travel there via plane, train, bus, or personal vehicle.

Chicago’s central location and the fact that it is accessible by many major interstates and highways make it easy to get there by car.

Be aware that there are several Illinois tollways as you drive into the city, so be sure to have spare dollar bills on hand.

If traveling from a farther distance, however, search for flights into either O’Hare International Airport or Chicago Midway International Airport.

How to Get Around Chicago

Chicago is a walkable city meaning that when staying downtown, the majority of the popular restaurants, sites, and attractions are all within walking distance to one another.

If staying downtown you simply do not need a car to get around once there.

For longer stretches, Uber vehicles are highly prevalent and can typically be found within 2 – 3 minutes of any given address.

In addition, Chicago is well-known for its convenient street system and its fantastic  public transit system .

Where to Stay in Chicago

If you’re planning a vacation in Chicago, IL, there are several options on  where to stay in Chicago .

Regardless, be sure to stay downtown so that you can do as little driving around as possible.

Choices downtown include staying within the Magnificent Mile, The Loop, or River North neighborhoods.

The Magnificent Mile is close to the John Hancock Building, Navy Pier, and upscale shopping.

The Loop is close to the Willis Tower and Millennium Park.

On the other hand, River North hotels are still within walking distance to major attractions but provide more budget-friendly options that often include pools and free breakfast.

Here are some of our favorite  Chicago resorts for families:

  • Embassy Suites Chicago Downtown Magnificent Mile
  • Embassy Sites Chicago Downtown
  • Courtyard Chicago Downtonw/Magnificent Mile
  • Homewood Suites Chicago Downtown/Magnificent Mile

Chicago Family Vacation: If You Have More Time

If you’re fortunate to be planning a Chicago 4-day itinerary, you’ll have time to do a few extra things.

The one area of downtown that we did not get to experience was the extremely popular Museum Campus which is home to several world-famous Chicago museums.

Places such as the Shedd Aquarium, the Field Museum of Natural History, and Alder Planetarium, are places that we will definitely visit during our next family vacation to Chicago.

The Museum of Science and Industry is another Chicago family favorite and should be considered if you like science and technology.

An important note is that both the Museum of Science and Industry and The Field Museum are both sensory-friendly Chicago activities for visitors with autism or sensory processing disorders.

[All Included in the Chicago CityPass ]

Thank you to Choose Chicago, Best Western River North, Chicago Architecture Foundation Center River Cruise aboard Chicago’s First Lady, Chicago Food Planet’s Signature Food Tour at Navy Pier, 360 Chicago and TILT, Art Institute of Chicago, Blue Man Group Chicago, and SafeHouse Chicago for hosting our family’s visits. I was not compensated for this Chicago 3 Day itinerary article. All opinions are my own. Jen

If you like our Family Chicago Vacation itinerary, here are our related posts to help plan your trip:

  • 25 Exciting Things to do in Chicago at Night
  • Famous Chicago Food: 5 Foods You Must Try During Your Visit
  • Top 5 Kid-Friendly Downtown Chicago Restaurants that Your Family Will Love
  • What to Wear in Chicago: A Visitor’s Guide For All Seasons
  • Top 10 Things to do at Navy Pier Chicago with Kids
  • Our United States Bucket List: 15 Exciting Places For Families to Go

*Before leaving, be sure to check our Travel Resources Page to find exclusive travel discounts and to book hotels, rental cars, and guided tours.*

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Jen Brommer is a family travel expert. She has been featured as an authority on several notable travel websites and is a member of the Family Travel Association (FTA), Midwest Travel Network, and TravMedia global media network.

A prominent content creator and influencer on Instagram, Jen has over 150K unique monthly blog readers from countries all over the world. She has spent the last 16 years planning fun, and hassle-free family vacations for her family of 5.

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  • Pingback: What to do in San Dieog with Kids: Perfect Itinerary | Travel With A Plan
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This looks like such a fun trip to Chicago! We did the same river cruise pre-kid and loved it. Definitely planning a trip to Chicago with my son in the near future!

Awesome! We loved it there! Hopefully you and your son can do some of these same things 🙂

What a fun trip to Chicago! I’ve had quite a few dog-friendly Chicago trips and we always have a great time. The Architectural River Cruise is a must! It’s such a wonderful way to view the amazing buildings.

I noticed that it was very dog-friendly! We love that about Duluth, MN too!

I would love to visit Chicago!

Yes, it is truly great! Let me know if you ever need additional tips!

As a (former) Chicago resident, I can honestly say this is a great itinerary! Portillo’s Chopped Salad is my favorite and I grab one anytime I’m passing through Phoenix as they actually have a couple of Portillo’s locations.

That is the best feedback ever! Thanks for sharing! I didn’t have that salad…but will have to when we go back!

I would love the opportunity to do more of Chicago. Navy Pier was a big highlight but i’d love to do some of this other stuff!

Yes, there is literally so much to see and do for all ages! We will definitely be returning soon!

We adore Chicago – saving this four our next trip!

Yay! This itinerary was flawless for us! Let me know if you return!

Chicago is one of my favourite cities in the USA, this post has got me desperate to return!

Basking in the memories, it makes me want to return too!

My brother isn’t that far from Chicago! We should make a weekend of visiting him and seeing the city. Thanks for all the tips!

For sure! You’ll love it! Plus, you’ll get to see your brother!

Saving this! We have one day in Chicago on our upcoming October trip with kids and I can’t wait! Thanks for the tips!!

Yay! So glad that you find is useful! Have so much fun there!

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3 Days in Chicago Itinerary How To Plan a Chicago Trip by JetSettingFools.com

3 Days in Chicago: Best Itinerary For A Trip To Chicago

Welcome to JetSetting Fools, here you will find our best travel tips for destinations worldwide. Some of the links on this site are Affiliate Links and if you use them to make a purchase, we may earn a commission. For more information, read our Disclosure Policy .

Looking to plan the best trip to Chicago, Illinois? Don’t stress – we have it covered! After visiting the Windy City on numerous occasions, we have created the Ultimate 3 Days in Chicago Itinerary. Including the best sights, must-do activities and local eats, our Chicago trip planner is all you need for a fantastic visit to Chi-town!

How To Plan A Trip to Chicago, Illinois

Planning a Chicago trip can feel overwhelming, but we are here to help! Chicago is steeped in riveting history, decorated with dazzling architecture and is famous for its food scene. While Chicago is bordered on the east by Lake Michigan, the city sprawls in all other directions.

Many of the top Chicago attractions are found in the very walkable downtown loop, and a few must-see Chicago sights are scattered further afield. We are sharing our top tips in a day-by-day Chicago 3-Day Itinerary so that you can plan a Chicago trip without worry.

Pro Tip:  Get (and stay) organized for your vacation to Chicago using our Trip Planning Printables !

3 Days in Chicago

Chicago is one of the best weekend destinations in the United States ! Visiting Chicago in 3 days is just enough time to see the highlights and get a taste of the city – and we squeeze just about all that we can into our perfect Chicago 3 Day Itinerary.

In fact, our trip plan is designed for a long weekend in Chicago – based on the assumption that visitors will arrive on Friday or Saturday and stay until Sunday or Monday. That said, our Chicago in 3 Days Itinerary can be used for trips on any days of the week (with just a few minor adjustments).

While we think three days in Chicago is a perfect amount of time for a visit, we know not all travelers are planning a 3-day Chicago trip. Therefore, we offer alternate Chicago itineraries – for shorter and longer trips – at the end of this article. Whether you are planning a 2-Day Chicago Itinerary, making plans for 4 days in Chicago or devising a Chicago 5-Day Itinerary trip plan, you can use our suggestions for your vacation!

What To Eat & Drink during your Chicago 3 Day Itinerary

Eating is one of the top things to do in Chicago in 3 days. The city is home to numerous legendary eateries – far too many to fit into one fun weekend trip in Chicago. To help, we have narrowed it down to the best Chicago food options.

Throughout our Chicago Three Day Itinerary, we highlight the most famous Chicago restaurants. Our food recommendations include classic eateries, Chicago’s best hot dogs, and – of course – iconic Chicago deep-dish pizza. For drinks in the Windy City, we feature locally brewed beer, swanky cocktail lounges and famous jazz bars. 

You will find all of our recommendations for food and drink sprinkled throughout our 3 Days in Chicago Itinerary.

Our Chicago Itinerary for 3 Days

Our 3-Day Itinerary for Chicago features the best of the city in an easy to follow day-by-day plan. At the end of the post, you will also find our tips for how to get there, where to stay and what to pack.

Our Chicago three-day itinerary includes everything you need to plan your ultimate trip to the Windy City. Save, Bookmark or Pin this post for your Chicago trip!

Day 1 of Your 3 Day Chicago Itinerary: City View, Park, Beach and West Loop

On the first day of your 3-day trip to Chicago, get settled into your accommodations (recommendations below) – then get an overview of the area. Next, explore the city’s best park and beach before setting off for a fun night in Chicago’s West Loop.

Chicago Itinerary by JetSettingFools.com

360 Chicago Observation Deck

Start your Weekend in Chicago Itinerary with the city’s best view! Zip to the top of 875 North Michigan Avenue – formerly the John Hancock Center  – to the 360 Observation Deck. The elevator ride only takes 40 seconds to travel 1,000 feet – so you should have no problem fitting the activity into your Chicago, Illinois trip plan!

Inside the 360 Observation Deck, visitors are greeted with incredible views of the Chicago skyline and Lake Michigan. Spend some time leisurely soaking in the view, sipping a drink at the bar or experiencing TILT – which claims to be the Highest Thrill Ride on the Planet. Buy your tickets now!

Historic Chicago Water Tower, Lincoln Park and North Avenue Beach

With your feet back on the ground, see some of the highlights of the City of Chicago. Walk to a historic landmark, through a beautiful park and along the shoreline on a Chicago beach.

The Chicago Water Tower still stands as a top Chicago landmark. Built in the 1860s, the tower is located on the famous Magnificent Mile. It is one of the few buildings that survived the 1871 Great Fire of Chicago. Although now in the shadow of skyscrapers, the tower is an important part of history and should not be missed by visitors to Chicago. 

Next up on your 3 Day Chicago Trip is the city’s best green space: Lincoln Park. Explore the myriad of paths that crisscross through the expansive lakeside Lincoln Park. If you are planning a trip to Chicago with kids, consider stopping at the Lincoln Zoo (it’s free!)! If the weather is cooperating, continue your walk on the sand at North Avenue Beach – and if it’s summertime, consider taking a swim in Lake Michigan!

Deep Dish Pizza for Lunch

For lunch, indulge in Chicago’s culinary creation: Deep Dish Pizza. Lou Malnati’s Pizzeria is a Windy City favorite known for their butter crust – and is a must-try during your 3 days in Chicago. The family-owned restaurant has several locations (including one just south of Lincoln Park).

That said, it’s not the only place to get gooey deep dish deliciousness on your weekend Chicago trip. There are dozens of highly acclaimed pizzerias serving up deep dish pies in Chicago. Giordano’s, Pizzeria Uno and Gino’s East are all good options for Chicago deep dish pizza. The Chicago Pizza and Oven Grinder Company, however, gets our vote and many rave reviews for their deep dish pizza and creative Pizza Pot Pies. 

Goose Island Fulton Street Brewery Tour

After lunch, continue to the next stop on your Three Days in Chicago Itinerary: The Chicago-born Goose Island Brewery. Established as a small city brewpub in 1988, Goose Island is now a globally recognized beer brand (thanks in no small part to it’s acquisition by Anheuser-Busch in 2011).

At the Fulton Street Brewery and Taproom, patrons are invited to take a brewery tour to witness the behind-the-scenes production process…and then sip delicious, fresh beer. Even if you skip the tour, this is a fun brewpub and should definitely be included on a beer-lovers three day Chicago Itinerary!

Time Out Market Chicago

We were first introduced to the concept of Time Out Markets in Lisbon, Portugal , where we were absolutely thrilled that they brought the best local chefs under one roof. At the Chicago Time Out Market, which is situated in the heart of the West Loop dining district, the idea is the same – and we think it’s a must for your Chicago Itinerary!

Visitors can order dishes from any of the carefully selected 18 Chicago chefs. The warehouse-style market encompasses 50,000 square feet of dining space – and includes 3 bars and a rooftop terrace.

The buzzing Time Out Market features Chicago classics, international fare and decadent desserts that are all well-recognized brands of the city.

A Night Out during Your 3 Day Itinerary Chicago

While patrons can linger at the Time Out Market bars, with only a weekend in Chicago, we recommend moving on to one of the hip bars in the West Loop (or beyond).

Best Bars for Day 1 of your 3 Days in Chicago

There is no shortage of hangouts in West Loop, so where you go depends on your taste. To help you decide, we’ve rounded up a short list of some of the fun bars you can add to Day 1 of your Chicago 3 Day Itinerary.

Blind Barber

Just a block west of the Time Out Market is Blind Barber, a barbershop by day…and a swank, 70s-style speakeasy by night.

Emporium Fulton Market

The fun Emporium Fulton Market is just down the street to the east – and features an array of arcade games and craft cocktails.

Lone Wolf Chicago

A favorite local neighborhood spot, the Lone Wolf is a classic and comfortable establishment to add to your Chicago night out.

Haymarket Brewery

If you are in search of Chicago craft beer, don’t miss Haymarket Pub and Brewery. They also feature live music on weekends.

Green Mill Cocktail Lounge

However, visitors who are planning a trip to Chicago and want to sip a cocktail inside a Chicago institution should leave the West Loop and head uptown to Green Mill Cocktail Lounge.

The iconic bar opened in 1907, was partly owned by Al Capone during Prohibition, has hosted famous singers – such as Billie Holiday – and now regularly features jazz and poetry nights. Just be prepared; it’s a bit north of the city, there is a cover charge, it’s cash only and seating is first come, first served.

Day 2 of Your Chicago Itinerary in 3 Days: The Loop, Architecture and Windy City Sports

On the second day of your Chicago in a Weekend Itinerary, explore top attractions on foot and by boat, then end the day in a classic northside neighborhood, maybe even watching a baseball game!

How To Plan a Chicago Trip by JetSettingFools.com

Breakfast At The Famous Lou Mitchell’s

For breakfast on Day 2 of your Chicago trip, indulge in a hearty Midwest-style meal at the iconic Lou Mitchell’s. For a 100 years, the diner has been serving up omelets and pouring coffee for hungry patrons. Definitely old school and a little quirky (they hand out Milk Duds), eating at Lou Mitchell’s is a Chicago must!

Union Station Chicago

Ease into your full day of Chicago sightseeing at the landmark Union Station. Opened in 1925, the station serves Amtrak and Metra commuter lines – and ranks as the busiest rail station in the United States outside of New York City . Occupying an entire city block, the classic Great Hall waiting room is at the center – and is recognizable from many popular Hollywood films including The Untouchables and My Best Friend’s Wedding.

The Loop Walking Tour

Spend the rest of the morning walking off your Midwest breakfast on a self-guided walking tour of the Chicago downtown Loop. The district features historic architecture, lush parks and intriguing artworks. Exploring this area is an absolute must when visiting Chicago.

Trip Planner Chicago Loop

Begin your discovery at the well-recognized Willis Tower (formerly the Sears Tower), which ranked as the tallest building in the world when it was completed in 1973. Visitors can soar to the 103rd floor Skydeck Chicago (be sure to buy your ticket in advance !). After visiting the Willis Tower, continue on your tour of the Chicago Loop.

Explore the following Chicago Loop sights (in order) and use this link to Google Maps for locations.

  • Daley Plaza (and Picasso’s Untitled artwork)
  • Miro’s Statue
  • Chicago Theater (and famous Chicago sign)
  • Old Marshall Field Building (and legendary clocks)
  • Chicago Cultural Center (and Tiffany Dome)
  • Millennium Park and Grant Park (Cloud Gate mirrored sculpture a.k.a. The Bean , Crown Fountain – then detour out of the park to see the historic Route 66 Begin sign and go one block west to see the famed Palmer House Hilton Hotel – Chicago Stock Exchange Arch, Buckingham Fountain)
  • Queen’s Landing
  • Lakeshore Trail  
  • Chicago Riverwalk (view The Wrigley Building and Tribune Tower across the river)
  • DuSable Bridge

Billy Goat Tavern For Lunch 

End the tour by crossing the DuSable bridge and walking north on Michigan Avenue to the Plaza of the Americas – then have lunch at Billy Goat Tavern. This iconic eatery is surely a highlight of any weekend trip to Chicago. 

Established in 1934, the Billy Goat Tavern opened at the Lower Michigan Avenue location in 1964 and has been serving their famous “Cheezborgers” ever since. The original owner was the historic instigator of the Chicago Cubs’ Curse of the Billy Goat and the tavern was the inspiration for the Olympia Café in 1970s Saturday Night Live sketches .

Chicago Architecture River Cruise

After lunch, hop on a boat for a different perspective of the Chicago skyline – it’s an absolute must for a summer Chicago weekend itinerary. Enjoy an entertaining hour-long river cruise along the three branches of the Chicago River. The on-board tour guide shares the history of the city and more than 40 buildings that you will pass along the way. Book your seat now!

Wrigleyville (and a Cubs Game)

Home to the much-loved Chicago Cubs (unless you’re from the South Side or St. Louis), Wrigleyville is a north side neighborhood packed with lively bars and fantastic eateries. The historic Wrigley Field is at the heart of the neighborhood – and attending a baseball game (regardless of who you’re rooting for) is a highlight of any itinerary for Chicago.

If the Cubbies are not playing while you are vacationing in Chicago, it is still worth visiting the neighborhood for dinner and drinks. Visit one of the famous Clark Street sports bars – like the Cubby Bear or Sluggers – for simple grub and drinks (or go for a gastropub dinner at Mordecai).

If the Cubs are away and seeing a baseball game is at the top of your list of things to do in Chicago, then check the South Side White Sox schedule.

Outside of the summer baseball season, there are numerous pro sports events that you could add to your three days in Chicago trip plan. Check schedules for the world famous Chicago Bulls (basketball), Chicago Bears (football), Chicago Blackhawks (ice hockey) and Chicago Fire (soccer).

Day 3 of Your Weekend in Chicago Itinerary: Walking Trail, Hot Dogs & Navy Pier

Wrap up your 3 Days in Chicago Itinerary with more sightseeing, eating and walking it off! Start the day at a cool urban park, embark on a local food tour, get a birds’ eye view of the city and end your Chicago tour itinerary at tourist hotspot, Navy Pier.

3 Days in Chicago by JetSettingFools.com

Walk Off the Food You’ve Eaten in Chicago in 3 Days

When we plan a trip to Chicago that includes gorging on the local fare, we also carve out time to walk it off. While our Weekend in Chicago Itinerary naturally includes a lot of walking between sights, there are two fabulous places to hit really stretch your legs: 606 Bloomingdale Trail and Lakefront Trail.

The 606 Bloomingdale Trail 

Similar to the New York City Highline and the Paris La Promenade Plantee, the Bloomingdale Trail at The 606  is a repurposed elevated train track-turned-public-park. Running three miles through four districts (Wicker Park, Bucktown, Humbolt Park and Logan Square) on Chicago’s northwest side, the walking trail features art installations and hosts local events.

We recommend walking The 606 from east to west. Churchill Field Park is a great place to hop on the trail. Pop into Mindy’s Bakery, run by famed Chicago chef Mindy Segal, for an incredible breakfast before starting your walk. Just be warned, there will likely be a line out the door – breakfast at Mindy’s is one of the top things to do in Chicago on a weekend – and it’s closed Monday – Wednesday.

Lakefront Trail

As the name suggests, the Lakefront Trail fronts Lake Michigan – and, for many visitors, walking along the shoreline is a highlight of a 3 Day Itinerary for Chicago. The trail stretches for 18 miles and can be used by bicyclists and pedestrians. From the path, there are fabulous views of Chicago and the shoreline. Hop on at any point and walk as far as you would like!

Famed Chicago-Style Hot Dogs

Your Chicago Trip Planner is not complete without consuming at least one hot dog. Chicago Dogs are noted for being ‘dragged through the garden’ – meaning, piled high with toppings that include mustard, onions, relish, tomatoes and a dill pickle spear sprinkled with celery salt (but never ketchup!). Unarguably, the place to get a Chicago Dog is at Portillo’s – a long-time, well-known chain that originated in the city (and has now expanded across the United States). 

In addition to hot dogs, Portillo’s also serves fabulous Italian Beef Sandwiches – another must-eat in Chicago! However, if you are just going after the beef, then go to Al’s #1 Italian Beef – an iconic Chicago eatery chain that was established in 1938.

Alternatively, Join a Chicago Food and Drink Tour

While we have included some of the top must-eat restaurants in our Chicago in a Weekend Itinerary, there is still more feasting to do! Rather than choosing one place for lunch on the last day of your 3 perfect days in Chicago, taste-test your way through the city. Join an expert guide in the local foodie scene to discover favorite haunts and classic fare including Deep Dish Pizza, Italian Beef, famous Chicago Hot Dogs and more. Get the details here!

Explore Navy Pier Chicago

Complete your Weekend in Chicago Itinerary with an afternoon at Navy Pier. Like Pier 39 in San Francisco , Navy Pier caters mostly to tourists, but a fun and enjoyable time is had by all. Featuring a wide array of restaurants, souvenir shops and art exhibitions, Navy Pier is a must-see in Chicago…and a great way to end your Chicago 3-Day trip!

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More Chicago Things To Do

We have outlined our best Chicago itinerary, including the top things to do when you visit Chicago in 3 days. Still, how to plan a trip to Chicago will depend on your specific interests. Therefore, we are sharing more fun things to do that you may want to add to your weekend trip to Chicago Itinerary.

Shopping on The Magnificent Mile

Visitors who want to go shopping in Chicago will find there is no shortage of stores! The best place to shop is on the famed Magnificent Mile, which is the section of Michigan Avenue that runs from the Chicago River north to Oak Street. The cosmopolitan street is lined with an astounding 460 retailers – from recognizable department stores to chic boutiques – and is a top destination for fashionistas planning a 3 Days in Chicago Itinerary.

Chicago Museums

With more than 65 museums in Chicago, there is certainly something for everyone. Whether it’s art, history or science that piques your interest, you can find a museum to include on your Chicago trip itinerary!

Chicago Trip Ideas: What Museums to Visit

When you plan trip to Chicago, it can be difficult to choose which museums to visit on your vacation. We are highlighting a few of the renowned museums to help you decide. 

Art Institute of Chicago: The city’s most famous art museum, the Art Institute is a top pick for 3 days in Chicago trips ( buy Skip-the-Line Tickets! ).

Museum of Science and Industry: The hands-on, family-friendly Museum of Science and Industry is a good museum to visit if you are planning trip to Chicago with kids. 

Museum of Contemporary Art: The fun and modern Museum of Contemporary Art is a fantastic museum to visit on a weekend getaway to Chicago. 

Shedd Aquarium: Whether you are planning a Chicago trip with family, as a couple or with a group of friends, the state-of-the-art Shedd Aquarium is a good addition to your Chicago vacation planner. 

The Field Museum: A fascinating museum of mummies and dinosaurs, the Field Museum is an excellent stop on a 3 day trip to Chicago. 

Adler Planetarium: If time permits in your itinerary, plan a day in Chicago that includes stargazing at the Adler Planetarium. 

Pro Tip : Save money and skip lines with a Chicago CityPass ! If you are planning on visiting more than one museum during your three days in Chicago, it will almost definitely save you money!

Go to a Theater Performance in Chicago

Need more ideas of what to see in Chicago in 3 days? Go to a show! Chicago has a vibrant theater district comprised of more than 250 theaters. From world-class productions to comedy acts, some of the best actors and comedians in the world have graced the stages in Chicago. 

Chicago Neighborhood Exploration

One of our favorite things to do in any city is explore the unique neighborhoods and districts. Throughout our Chicago weekend trip itinerary, we have featured some of the top Chicago districts – but we by no means covered them all. Some of the other places to explore in Chicago are Chinatown, Little Italy, Lincoln Park, Wicker Park, Boystown and Roscoe Village.

What To See Do Eat 3 Days in Chicago, Illinois USA by JetSettingFools.com

How Many Days in Chicago?

We think 3 days in Chicago is the perfect amount of time to get acquainted with the city…but we would have no problem entertaining ourselves for a week in Chicago – or longer!

How many days you spend in Chicago will ultimately depend on your interests, budget and availability.

Sample Chicago Itineraries 

We have outlined a perfect plan for a long weekend in Chicago – but what if your trip plans include more (or fewer) days? No worries! Using our 3-Day Chicago Weekend Itinerary as a base, we are sharing our best suggestions for longer and shorter trips.

1-Day Chicago Itinerary

Planning a Chicago in One Day Itinerary is not easy. The city has so many iconic sights and delicious things to eat that it is difficult to pick and choose which ones to include in your Chicago trip plan. However, if one day is all you have, then we suggest making the absolute most of it!

Chicago 1 Day Itinerary Trip Plan

For us, an ideal One Day in Chicago Itinerary would follow Day 2 in our above plan of what to do in Chicago in three days. However, unless you are passionate about baseball, rather than going to Wrigleyville we would recommend spending the evening on Navy Pier or in West Loop.

Chicago Itinerary 2 Days

With 48 hours in Chicago, visitors can plan a Chicago 2-Day Itinerary that is succinct and hits almost all of the highlights.

Chicago 2 Day Itinerary Trip Plan

If you are planning a 2-Day Itinerary for Chicago, we suggest following Days 2 and 3 of our outlined plan for what to see in Chicago in 3 days. Again, if the Cubs were not playing, we would skip Wrigleyville and spend the evening in West Loop, even squeezing in the Goose Island Brewery Tour if possible.

Chicago Itinerary 4 Days

Planning a 4-Day Chicago Itinerary allows for a lot more sightseeing – including many of the museums that we skipped in favor of neighborhood exploration. 

Chicago 4 Day Itinerary Trip Plan

To organize an ideal 4 Days in Chicago Itinerary, we would follow our Chicago 3-Day Itinerary – then, on the last day, we would use the CityPass to visit the top museums, including The Art Institute, Field Museum, Shedd Aquarium and Museum of Science and Industry.

Chicago Itinerary 5 Days

Spending 5 days in Chicago allows for a lot more adventures at a somewhat leisurely pace.

Chicago 5 Day Itinerary Trip Plan

To plan a perfect 5-Day Chicago Itinerary, we recommend following the above outlined Chicago 4-Day Itinerary – then, on the last day, spend the morning discovering a new neighborhood, go shopping on the Magnificent Mile in the afternoon and attend a theater performance in the evening – then get a drink at the Lobby Bar in the posh Palmer House for a nightcap.

Tips For Planning Your Trip to Chicago

Now that you know what to do in Chicago in 3 days, we have a few more essential tips for your trip!

Organize your Chicago Travel Plan

There is a lot more to Chicago trip planning than determining what to see and do. Don’t worry – we share our top tips for planning a vacation in Chicago – from how to get there to what to pack – in the next sections. 

As you research Chicago vacation ideas and start making reservations, make sure you stay organized. A useful travel planner – like our Printable Travel Planner – will help you keep track of all the details of your perfect Chicago travel itinerary! 

Travel Planner Printables by JetSettingFools.com

How To Plan Chicago Trip Budget

A trip to Chicago, Illinois can be expensive – but it doesn’t have to be. Travelers who are planning to spend a weekend in Chicago on a budget have many options for exciting entertainment. We suggest skipping sights with high-priced tickets and partaking in many of the cheap and free things to do in Chicago. 

Get our tips on how to plan the best budget trips – plus get our free Vacation Budget Planner – to help plan your budget Chicago, Illinois trip! 

How To Get to Chicago

An essential consideration for your Chicago trip itinerary is how to get there! Chicago can be reached by car, bus, train or plane. On our trips to Chicago, we have always arrived via plane.

Flying To Chicago

There are two major Chicago airports: O’Hare International (ORD) and Chicago Midway (MDW). Both airports have their pros and cons – O’Hare is an enormous airport serviced with flights from around the world ( London , Hong Kong , Tokyo , Munich , etc.), but is far from the city center. Alternatively, Midway dominated by Southwest Airlines and they service mostly US domestic destinations, but is much closer to downtown Chicago.

Both airports are connected to downtown Chicago via public transport (the Blue Line from ORD and the Orange Line from MDW), but visitors can also use taxis, Uber or private transport , too. 

Start your search for the best airfare and flight times on SkyScanner  – but first read our Top Tips for Finding Cheap Flights .

Trip To Chicago by Train

If you are traveling to Chicago from another city that is serviced by Amtrak, then you can also plan a Chicago 3 Days Itinerary with arrival by train. That said, the journey will likely take longer and could even be more expensive than flying – so bear that in mind as you make your trip plans! 

Getting Around Chicago

Downtown Chicago is very walkable – but getting to the districts outside the city center require transportation. Besides your own two feet, visitors have options when it comes to getting around Chicago – from the ‘L’ train to CTA buses to bikes to scooters to Uber and Lyft. 

Public Transportation

Chicago has one of the most extensive public transportation systems in America and makes getting around Chicago fairly easy. Both the ‘L’ train and buses have extensive networks. The affordable fares can be paid using a Ventra account – and both 1-Day and 3-Day flat fare tickets are available for your Chicago visit. Find Chicago Transit fare info here . 

More Ways to Get Around Chicago

That said, using Uber or Lyft is likely much more convenient – and if traveling in a group – not too expensive.

We do not recommend driving a car during your Chicago weekend itinerary; parking is a hassle and can cost a bundle.

Chicago Hop On Hop Off

The Chicago Big Bus provides an excellent service for travelers who want to easily get from one tourist site to the next. The Hop On Hop Off Chicago buses are double-decker, open-air vehicles that make stops at all top attractions – and include informative on-board commentary! Buy your ticket!

Where To Stay in Chicago

Although there are hundreds of places to stay in Chicago, for your Chicago vacation itinerary, we recommend choosing downtown accommodations.

Chicago Hotels

If you are going to splurge for 3 nights in Chicago, there is no better place than The Palmer House Hilton . The historic hotel, featuring a gorgeous lobby, is in a prime location within the Theater and Financial Districts near Millennium Park.

That said, there are hotels in Chicago that fit every budget and style. To find the perfect Chicago hotel for your stay, start your search on Booking.com – like we do. Use the filters to select the hotel amenities that are most important to you – and use the map to find the best location. Be sure to read all of our best tips for booking hotels !

3 Day Trip Chicago Vacation Rentals

In our travels, we often use Airbnb to find affordable apartments in the places we visit. In fact, we have found that Airbnb is sometimes less expensive – and offers more space – than most hotel rooms.

However, this is not always true on short stays. Be sure to check the extra fees when booking a short trip – like 3 days in Chicago – before confirming your Airbnb stay.

What To Pack For Your Chicago Trip

We have a few final tips and packing hacks for what to pack for your 3 perfect days in Chicago. Need a packing checklist? Grab your FREE Printable Packing Checklist here !

Weather Appropriate Clothing for Your Chicago 3 Day Itinerary

What you pack in your suitcase for a trip to Chicago will depend on the season. Winters can be frigidly cold, summers are often unbearably humid, springtime is wet and autumn is likely to be brisk, hot or soggy. So yes, the frequent weather changes make planning what to pack for your trip a bit of a conundrum.

If you are taking a Chicago summer vacation, pack loose-fitting clothes, a wide-brimmed travel hat and sunscreen . In the wintertime, you will need a winter coat, cozy cap  and gloves . And, if traveling in the spring or fall, make sure to bring a packable raincoat and travel umbrella . Because the weather can fluctuate, it is best to pack clothing that can be layered and carry a great day bag for quick wardrobe changes and all your everyday essentials .

Walking Shoes for Your Itinerary for Chicago

Our Chicago 3-Day Trip Itinerary includes a ton of walking! We recommend wearing a pair of comfortable walking shoes for trekking around the city. I like to wear these lightweight shoes by Columbia and Kris prefers wearing his Merrell trail shoes for city walks.

Travel Camera

Chicago is incredibly photogenic – and, if you are anything like us, you will be snapping a lot of pictures during your three days in Chicago. Instead of using your cell phone camera to capture the sights, we recommend upgrading to a real camera . We travel with a DSLR Canon Rebel and use an everyday 18-135mm lens . The camera comes bundled with tons of accessories – so it is perfect budget camera for beginners!

US Travel Insurance for Your Chicago Itinerary 3 Days

Travel insurance can be useful on all kinds of trips – even a long weekend in Chicago. It can cover unfortunate situations, like cancelled trips, lost luggage and more. Check rates and coverage on World Nomads .

Start planning your trip to Chicago, Illinois ! Search for the lowest airfares , the best accommodations and fun things to do …then start packing !   Want more travel planning tips? Head over to our Travel Planning page for more information and tips on traveling – and for country-specific information, take a look at our Travel Guides page !

Visit More Top Destinations In The USA

Planning other trips in the United States? Use our detailed guides to discover the best of cities across America (and some Underrated US Destinations ). In fact, we wrap up our top picks for the best places to go in our guide, 22 Weekend Getaways in the US !

Best Weekend Getaways in USA Top 22 Destinations

Already have a destination in mind? We offer comprehensive guides for Phoenix , Columbus OH , Indy ,  Portland , Austin , Seattle , Boston , Denver and San Diego – to name a few! 

Up for a US road trip? Use the tips in our articles for the Oregon Coast , Columbia River Gorge , the California Coastline and through amazing Montana.

Find all of our tips for traveling in the United States on our USA Travel Destinations Page . 

We Want To Know: Do you have any advice on how to spend 3 days in Chicago? Is there anything you would add to our Chicago Itinerary? Give us your best tips on how to plan a Chicago trip in the comments below! 

Click here for a Free Vacation Budget Planner Banner by JetSettingFools.com

Pin it! See all of our travel pins on our JetSetting Fools Pinterest Board .

3 Days in Chicago Itinerary Plan a Chicago Trip by JetSettingFools.com

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St. Joseph lighthouses

The best day trips from Chicago

Explore small-town breweries, bakeries and artisan shops when you embark on these easy day trips.

Jeffy Mai

You don’t have to go far or spend a lot of money to enjoy a nice escape from Chicago. A simple day trip offers a fun change in scenery and is cheap and easy. Luckily, there are many exciting destinations within driving distance or accessible by train that provide the perfect getaway. Spend an afternoon soaking up the rays on beaches along Lake Michigan, go hiking near Chicago in a state park or sample a variety of beers and cheeses up north in Wisconsin. The attractions are endless, ranging from amusement parks and Japanese gardens to museums and historic lighthouses. So whether you’re low on PTO or just trying to keep travel costs down, check out our guide to the best day trips from Chicago to explore everything the Midwest has to offer.

RECOMMENDED: The best weekend getaways from Chicago RECOMMENDED: The most unique day trips from Chicago RECOMMENDED: The best Chicago staycation ideas

An email you’ll actually love

Top day trips from Chicago

Milwaukee, WI

1.  Milwaukee, WI

Driving time from Chicago: One and half hours

Getting to the Cream City requires a painless drive, but if you plan to fully indulge, ditch the car and hop on the BYOB-friendly Amtrak, which will deposit you in the heart of the city in an hour and a half. Start your day with a stack of pancakes and a round of mimosas at Sweetdiner . Meander around the Historic Third Ward and hop into home decor shops like The Home Market  or fun specialty shops like MOD GEN . Seek refuge and treats at the Milwaukee Public Market , where you’ll find a hodgepodge of the city’s best vendors, including blends from The Spice House , seafood from St. Paul Fish Company , hand-dipped chocolate from Kehr’s Candies  and vino from Thief Wine Shop & Bar . Before catching a train home, walk off the day with a trek along to Lakeshore State Park , a unique 22-acre urban oasis that juts out from the shoreline.  

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2.  Fennville, MI

Driving time from Chicago:  Two hours and 20 minutes

Many Chicagoans wait until fall to venture up to western Michigan’s fruit belt. But there’s a compelling argument to be made for hitting the area a couple of months earlier, when the countryside is tranquil and stone fruits like peaches and cherries are ripe for picking. The petite town of Fennville is a great base for tasting the region’s sweet bounty in a host of iterations. Start off with a slice or two of the good stuff at local favorite Crane’s Pie Pantry , a bakery, restaurant and winery housed in a 150-year-old barn. From here, a five-minute drive will deliver you to Virtue Cider , founded by former Goose Island brewmaster Greg Hall. Reserve a spot for a guided trail tour that includes a glass of cider. Finally, make your way to Salt of the Earth for wood-fired pizza and seasonal dishes made from scratch with local and sustainable ingredients.

South Bend, IN

3.  South Bend, IN

Driving time from Chicago:  One hour and 45 minutes

There’s more to South Bend than Fighting Irish football. Check out the city’s cultured side with an afternoon visit to the History Museum , a stately Victorian mansion that was once home to the family of local industrialist and inventor James Oliver. From there, browse the local bounty at the South Bend Farmers' Market , where you can shop everything from artisan breads and doughnuts to farm-fresh fruits and veggies. When hunger strikes, head to  Café Navarre , an upscale dining spot housed in a repurposed '20s-era bank. 

Madison, WI

4.  Madison, WI

Driving time from Chicago:  Two and half hours

Located on an isthmus between two lakes, Madison is a city that’s filled with beautiful sights—in addition to all the cheese and beer you’ve heard so much about. Begin your visit with a scenic tour of the college town on two wheels. You can rent a bike from dozens of BCycle stations , allowing you to make 30-minute trips. The Capital City trail winds around Lake Monona (the smaller of the two lakes) and provides plenty of picturesque stops for an Instagram snapshot of the skyline. Now, onto that cheese and beer: To drink like a local, head for The Malt House , a “craft beer oasis” that dates back to the Civil War era and boasts taps from local brewers like New Glarus and Central Waters. Head for Capitol Square to visit Fromagination , where you’ll find artisanal Wisconsin cheeses and knowledgeable cheesemongers to help you make a decision. Take an evening to visit the Memorial Union   Terrace , a lakefront space on the University of Wisconsin campus where you can enjoy brats, beer and live music during the summer months. 

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5.  Gurnee, IL

Driving time from Chicago:  One hour

Located right off I-94, the village of Gurnee is a shopping and entertaining hub that draws 23 million visitors each year—including plenty of nearby Chicagoans. Start your day by fueling up with the brunch buffet at The Chocolate Sanctuary , where you can pile your plate with housemade bagels with lox, shrimp cocktail and chocolate-dipped strawberries. Spend some time digesting while you stroll around Gurnee Mills , which hosts more than 160 stores selling everything from sporting goods to home decor. Thrill seekers won’t want to miss Six Flags Great America , where you’ll find high-speed roller coasters and intense drop rides. On a hot day, you’ll want to plunge down the water slides and splash around the wave pool at Hurricane Harbor. If you can resist indulging in funnel cakes or turkey legs at the park, save your appetite for Primo Italian American Cuisine , where the dinner menu features black truffle ravioli and a tomahawk ribeye. Those visiting on a Friday can end the night with live music in The Parlor, Primo’s speakeasy-style lounge.

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6.  Oglesby, IL

Driving time from Chicago:  Two hours

It may not be the mighty Colorado, but Oglesby’s Vermillion River offers the best rafting you’re liable to find within a quick jaunt from Chicago. A 9.5-mile run with Vermillion River Rafting will shoot you over 14 rapids, most of them class I and II. After you’ve handed over your paddle, hop in the car and head up the road to Starved Rock Lodge , where you can catch your breath and lunch on casual fare like burgers or a strawberry pecan salad at the Back Door Lounge. When you feel sufficiently refreshed, hit the hiking trails at adjacent Starved Rock State Park to spot dramatic waterfalls and explore cool glacial canyons. Unwind from your nature adventures by grabbing a nostalgic treat at The Rootbeer Stand   or check out "farm to foam" at The Lone Buffalo by Tangled Roots Brewing Company  in nearby Ottawa. 

St. Joseph, MI

7.  St. Joseph, MI

Golden, sandy beaches and a picturesque shoreline attract visitors to St. Joseph and its twin city Benton Harbor. You can spend an entire day out on the water with a rental from Blue Water Boat Rentals , or walk over to the St. Joseph Lighthouses — guided tours are available. If you’re hungry, you won’t have to wander far for good grub, as Silver Beach Pizza —located inside a century-old train depot—slings dependable tavern-style pies. Oenophiles, hit up a variety of vineyards and tasting rooms on the Lake Michigan Shore Wine Trail for some fine Midwestern pours.

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8.  Harbor Country, MI

Driving time from Chicago:  One and a half hours

Just across the Indiana border, Michigan’s lakeside “Harbor Country” is only an hour and a half drive from downtown Chicago. Start at the north end, in Sawyer, where you can visit the original taproom of Greenbush Brewing Co.  Pair a pour of Star Chicken Shotgun IPA with some barbecue or Cajun fare. Up next, take the Red Arrow Highway down the lakeshore for great shopping, like hunting through the Harbert Antique Mall . Head back inland to the artsy community of Three Oaks to finish your day at Journeyman Distillery . A $13 tour and tasting nets you samples of 12 different spirits made in the converted corset factory. Plan to sit down for a meal at the distillery’s Staymaker restaurant afterward; you’ll need some food before getting back on the road to Chicago. 

Kenosha, WI

9.  Kenosha, WI

Driving time from Chicago:  One hour and 15 minutes

About an hour north of Chicago sits this Wisconsin town filled with a plethora of things to do. Within a mile radius of the downtown area are five museums—you can gaze at dinosaur fossils and learn about the link between the prehistoric reptiles and birds at the Dinosaur Discovery Museum , or explore how the Civil War affected people on the western front at the Civil War Museum . During spring to fall, visit the Southport Lighthouse and climb 72 steps to the top for unparalleled views of Kenosha and, on a clear day, the Chicago skyline. If it’s summertime, you must check out the Bristol Renaissance Faire , where you’ll find a recreated 16th century port city populated with fairgoers dressed as knights, maidens and much more. After you’ve worked up an appetite, head over to Frank’s Diner , an almost century-old restaurant set inside an old railway car. And don’t forget to grab some cheeses and New Glarus beers at the famed Mars Cheese Castle on the way home.

Rockford, IL

10.  Rockford, IL

Situated less than 100 miles northwest of Chicago, Rockford is a surprisingly plentiful road trip destination for families. If the kids are in tow, start the day with a visit to the Discovery Center Museum , which boasts more than 300 hands-on exhibits focused on everything from light and art to color and electricity. For a dose of fresh air and nature, wander through the Anderson Japanese Gardens , a breathtaking 12-acre oasis that's filled with winding pathways, koi-filled ponds, and colorful plants. Everyone in the car will find something to love at Prairie Street Brewing Company , where bar food is elevated through dishes like Korean street tacos, Cajun mac ‘n cheese and wild mushroom quesadillas. Pick up a few cans of Screw City Light—with notes of fresh-baked bread—to take home and extend your day trip. 

Cedarburg, WI

11.  Cedarburg, WI

Located just 20 miles north of Milwaukee, Cedarburg is an ideal place to wind down and take things slow. The charming small town is brimming with old-world architecture, friendly Midwesterners and culture galore. If you can, plan your trip around one of the town’s seasonal events, with options including the Wine & Harvest Festival and Oktoberfest —all of which offer ample opportunities to meet local vendors and sample their wares. When you’re not rubbing elbows with the close-knit community at a street fest, make time to walk around the Cedarburg Art Museum , which hosts exhibitions from Wisconsin artists inside a former home that was designed in 1898. If wine bars are more your scene, head to Cedar Creek Winery , where you can sip your way through a $10 wine fight or enjoy a seasonal wine and cheese tasting for $25. On your way out of town, make one last stop at Amy’s Candy Kitchen to grab a hand-crafted caramel apple for the road. 

Kankakee County, IL

12.  Kankakee County, IL

Driving time from Chicago:  One and half hours

The Kankakee River has been a treasured area for centuries, occupied by the Illini and Miami tribes in the 17th century. Kankakee River State Park surrounds the river for about 11 miles, totaling to 4,000 acres of protected land. It’s a popular spot for fishing, canoeing, hiking and bicycling. Frank Lloyd Wright fans can visit the B. Harley Bradley House , built in 1900 and billed as the architect’s first Prairie Style home. Bring the kids to Perry Farm Park , which features a children’s museum, nature trails, playground and picnic areas. 

Oak Park, IL

13.  Oak Park, IL

Drive time from Chicago:  Half an hour

You can't call yourself a Frank Lloyd Wright fanatic until you've spent the day in Oak Park, where you'll find the famed architect's home and studio as well as a smattering of other Prairie-style abodes he designed. If it's your first time, book a tour through the Frank Lloyd Wright Trust . Now that you've worked up an appetite, grab brunch or dinner at Maya del Sol , where margaritas flow like water and the ceviche is tops. Have time for one last stop? Grab a seat at Kinslahger Brewing Company , a small but mighty taproom pouring lagered brews. 

Grand Rapids, MI

14.  Grand Rapids, MI

Driving time from Chicago:  Three hours

Summer and fall are peak seasons to visit Grand Rapids, but you’d do best to plan ahead and book your visit during ArtPrize , an international art competition in September and October when art is displayed in museums, bars, public parks and hotels. Regardless of when you go, Grand Rapids has you covered on the beer front with dozens of breweries—so be sure to bring a designated driver. First stop: Brewery Vivant for poutine and a German- or Belgian-style beer. A quick 10-minute drive will put you in the middle of downtown, where you should find parking and hoof it a while. Stop at Madcap Coffee for a post-beer pick me up before heading to City Built Brewing for creole bites and a range of beers for every palate. Finally, grab your car and head to Butcher's Union  for a dinner complete with prime cuts of beef and pours of whiskey.

New Buffalo, MI

15.  New Buffalo, MI

Driving time from Chicago:  One hour and 15 minutes

A charming beach town in Harbor Country, New Buffalo is popular during the warmest months. Escape the crowded Chicago lakefront and head for the sandy shores of the Mitten State, where the water’s warmer and clearer. Soak up some rays and then stroll down Whittaker Street to peruse cute shops and art galleries. Book a spa treatment at The Harbor Grand Hotel for a re-energizing experience; adventurers can rent a kayak or paddleboard from Third Coast Paddling and go exploring on the Galien River. When you need to refuel, grab a seat on The Stray Dog Bar & Grill’s bustling patio or sink your teeth into a big, juicy burger from Redamak’s . But make sure to save room for unique ice cream flavors, like Mackinac Island Fudge and Jacked Up Tennessee Toffee, at Oink’s Dutch Treat .

Monroe, WI

16.  Monroe, WI

If your cheese preferences embrace the pungent, you’ll find yourself in good company in charming Monroe, Wisconsin, gateway to a region teeming with cheesemakers specializing in varieties like Swiss and nostril-tingling Limburger. For some context, begin your day at the National Historic Cheesemaking Center , where you’ll get a crash course in south central Wisconsin’s cheesy history. Next, head to the Alp and Dell cheese store to browse more than 100 varieties of cheese, mostly from local producers, and all the wine, beer and sausage you’d want to pair them with. When you’re ready for lunch, make your way to the unapologetically old-school Baumgartner’s Cheese Store & Tavern on Monroe’s pleasant courthouse square and order the infamous specialty: a slab of Limburger on rye crowned with mustard and sliced red onions. For a chaser, stroll around the block to Minhas brewery. 

Lemont, IL

17.  Lemont, IL

Driving time from Chicago: One hour

The Village of Lemont developed as part of the construction of the canal linking the Illinois River and Lake Michigan, which also led to the discovery and development of the limestone quarries used to supply materials for iconic Illinois buildings like the Chicago Water Tower. Today, you can hop on the Metra and visit the Heritage Quarries Recreation Area , where you can walk, bike or fish along the I&M Canal (just be sure to look out for the many water birds drawn to the area). If you’re hoping for a bit more excitement, visit The Forge: Lemont Quarries . The adventure park features laser tag, a zipline and ropes courses for all ages and skill levels. Afterwards, head to the village’s historic downtown area to visit Pollyanna Brewing Company and try The Full Lemonty, their signature golden ale. You can also find the brewery’s beer on tap at Wooden Paddle , where you can watch your wood-fired pizza and other small plates being prepared before they hit your table.

Holland, MI

18.  Holland, MI

Driving time from Chicago:  Two and a half hours

Once a stronghold of Calvinist separatists who arrived here from the Netherlands in the mid-19th century, the town of Holland continues to celebrate its Dutch heritage. To go Dutch for the day, start off with a breakfast of flaky, almond paste-filled bankets and house-roasted coffee at deBoer Bakkerij . Afterward, head across town to Veldheer Tulip Gardens , where five million of the eponymous flowers explode into bloom each spring. When hunger hits, make your way downtown for lunch and a beer at New Holland Brewing , one of the Midwest’s best-loved brewpubs. (Not sure what to sip on? Look for limited-release variations on brewery fave Dragon’s Milk, a bourbon barrel-aged stout, enriched with ingredients like cocoa nibs and peanut butter.) Wrap up your trip with a leisurely stroll around Windmill Island Gardens , a picturesque park centered around a 250-year-old Dutch windmill purchased by Holland residents in the 1960s. 

Long Grove, IL

19.  Long Grove, IL

Driving time from Chicago:  45 minutes

Located 35 miles northwest of Chicago, Long Grove was founded in the 1800s by German farmers, and many of the town’s original homes and buildings are still standing. Try to visit Long Grove during one of its many delicious festivals such as Apple Fest or Strawberry Fest , when local chefs and other vendors flock to the historic downtown area to offer numerous versions of the spotlighted food. Stop by  Buffalo Creek Brewing and have a beer in their Bavarian-style taproom or in the Biergarten, which hosts live music and food trucks during the summer. Before you hit the road, swing by Long Grove Confectionery to pick up some peanut brittle or their signature Giant Myrtle, made with roasted pecans or cashews topped with caramel and milk or dark chocolate.

Lake Geneva, WI

20.  Lake Geneva, WI

Lake Geneva has long been an accessible weekend destination for wealthy suburban Chicago families. But no matter your budget, a quick retreat to this idyllic vacation town is sure to be a blast. The town rests on Geneva Lake, an 8-square-mile body of water made for summertime fun. First things first: Get out on the water. Rent a kayak or paddleboard from Clear Water Outdoor , or take a wake surfing private lesson at Gage Marine . If you can’t get your sea legs, trek a portion of Lake Geneva’s 21-mile circumference on the Geneva Lake Shore Path and gawk at the century-old mansions that rest on the shore. When you’re hungry, Egg Harbor Café and Simple Cafe , both in the town center, offer delicious, no-fuss diner eats. If you’re feeling spendy, Baker House , a 19-century mansion-turned-hotel, offers a popular Champagne brunch with waterfront views. 

Evanston, IL

21.  Evanston, IL

Driving time from Chicago:  40 minutes

If you're short on time but craving a day away from the city, hop on the Purple Line and head to Evanston. The sweet college town is located just a few miles north of Chicago, which means you can explore the day away and still be home for dinner. Start the morning at the otherworldly Baha'i House of Worship , an architectural gem located a few miles north in Wilmette. Wander the pristine grounds before stepping inside the functioning temple, one of the oldest of its kind in the world. Up next: Fill up on colorful macarons, cakes and doughnuts at Bennison's Bakery before checking out the outdoor exhibition at the Block Museum of Art and taking a free art walk to see the 16 sculptures placed in public spaces on Northwestern University’s campus. Don't get back on the train without grabbing a brew from Temperance Beer Co. If you have the time, take a $10 brewery tour that includes samples and a souvenir pint glass. 

Michigan City, IN

22.  Michigan City, IN

If you’re car-less, this small city is a perfect option for a day trip from Chicago. Hop on the Amtrak at Union Station and you’ll be in Michigan City in just over an hour. Or, take the South Shore Line and you can hop off right at the Indiana Dunes National Park , 15 miles of gorgeous sand dunes on the southern shore of Lake Michigan. Michigan City proper, too, is filled with great things to do. Visit Washington Park where you can picnic on the beach or check out the lions, wolves and other animals from around the world at the Washington Park Zoo . Hungry? Walk over to Shoreline Brewery , a gem of a microbrewery with a rotating selection of beers on tap and tasty pub grub. You can also sample local flavors at Fiddlehead , which serves high-quality comfort food including fried lake perch and grass-fed beef burgers. 

Galena, IL

23.  Galena, IL

Driving time from Chicago:  Three hours

While this city on the Mississippi River might be best known for its resorts, you don’t need to stay the night to enjoy its mix of historical sites and outdoor activities. Start your day with brunch at Otto’s Place , where you can enjoy biscuits and gravy featuring housemade buttermilk biscuits and locally sourced sausage with a Bloody Mary or mimosa. Head across the Galena River to Nuts Outdoors and rent an electric bike to ride along the trails and into town. Take a tour of the city’s proudest attraction, the Ulysses S. Grant Home , which was gifted to the 18th president when he returned from fighting in the Civil War. If you want to learn more, you can visit the Galena & U.S. Grant Museum , which also features an offsite working blacksmith shop. That history is also on display at Galena Brewing Company , where you can sip Ult’s Dark oatmeal stout while listening to live music and feasting on a bison burger or a giant pretzel with beer cheese and house mustard.

Fairbury, IL

24.  Fairbury, IL

Observant Chicago foodies may have noticed a couple of names popping up over and over again in the menu sourcing notes that have become de rigueur in these locavore-obsessed times: Kilgus Farmstead (for dairy) and Slagel Family Farm (for a range of meats). Turns out, our favorite chefs’ favorite suppliers sit just a three-mile hop from each other in the central Illinois town of Fairbury. On an hour-long tour of Kilgus , you’ll get acquainted with the farm’s herd of sweet, doe-eyed Jersey cows, learn the ins and outs of milking, and sample freshly spun soft-serve. Bring a cooler and hit the on-site store for Kilgus dairy and meat as well as goods like eggs and honey from nearby producers. Slagel has teamed up with chefs from notable Chicago restaurants to put on a program of farm dinners throughout the summer and fall. After an interactive tour and a butchering demo, you’ll retire to a picturesque barn for the main event, a family-style, BYOB meal prepared by the guest chef. 

New Glarus, WI

25.  New Glarus, WI

Driving time from Chicago: Two and a half hours

Chances are you’ve already heard of New Glarus thanks the town’s eponymous brewery — which offers self-guided tours Monday through Friday and a lovely beer garden—but there are plenty of reasons to visit “America’s Little Switzerland” other than beer.  This charming, walkable town features a variety of tempting shops, hearty restaurants and themed events celebrating the town’s Swiss history and culture like the Heidi Folk Play Festival   in June . Be sure to grab a nut horn at the New Glarus Bakery , and get your fondue fix at the Chalet Landhaus restaurant. If you visit between May and October, don’t miss the seasonally-open Swissland mini golf course, featuring Alpine-themed obstacles and friendly goats. 

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26.  Spring Green, WI

Driving time from Chicago: Three and a half  hours

Despite boasting a population just shy of 1,700 people, this town west of Madison has a lot going on. Most visitors are here to visit one of two sprawling complexes: Taliesin , the estate and studio of legendary architect Frank Lloyd Wright, or the infinitely weirder House on the Rock , the brainchild of artist Alex Jordan where curious travelers can explore rooms on rooms of infinity mirrors, dollhouses, nostalgic cars, circus ephemera and the world’s largest indoor carousel. When you’ve had your fill of architecture or funky assorted collections,  get a taste of traditional Wisconsin hospitality at Arthur’s Supper Club . Theater buffs can take in a show at the American Players Theatre .

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Axios

Your guide to St. Patrick's Day parades in Chicago

Chicagoans love St. Patrick's Day so much they hold at least five big free celebrations.

  • With a little luck — and this guide — you could enjoy several of them over the next week.

Today: St. Patrick's Day at Gallagher Way features Irish dancing, music, lessons, face painting, Irish coffee, beer and lots of Guinness (11am-3pm).

Saturday, March 16: Watch the dyeing of the river between Columbus Drive and State Street starting at 10am.

  • The downtown St. Patrick's Day Parade steps off at Columbus and Monroe at 12:15pm featuring bands, performers, dancers and lots of politicians for about three hours.

Sunday, March 17: Catch the two-hour South Side Irish St. Patrick's Day Parade stepping off at noon from 103rd and Western and heading south.

  • Also at noon the Northwest Side Irish Parade celebrates its 21st year with dancers, musicians and family fun stepping off from Onahan Elementary School (6634 W. Raven).
  • Check out our locals' guide to enjoying both the South and Northwest Side parades .

Get more local stories in your inbox with Axios Chicago.

Your guide to St. Patrick's Day parades in Chicago

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